CN113038824A - Compounds and formulations for protective coatings - Google Patents

Compounds and formulations for protective coatings Download PDF

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CN113038824A
CN113038824A CN201980071772.5A CN201980071772A CN113038824A CN 113038824 A CN113038824 A CN 113038824A CN 201980071772 A CN201980071772 A CN 201980071772A CN 113038824 A CN113038824 A CN 113038824A
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alkynyl
alkyl
group
alkenyl
composition
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CN113038824B (en
Inventor
S·布拉登
C·霍兰德
L·佩雷斯
M·李
G·罗德里格斯
D·散多瓦
B·索尔坦萨德
E·博世
E·布罗德贝克
C·弗拉泽尔
C·赫尔南德斯
S·考恩
J·博金斯
J·罗格斯
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Apeel Technology Inc
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Apeel Technology Inc
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Priority claimed from US16/427,219 external-priority patent/US20200068912A1/en
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    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01GHORTICULTURE; CULTIVATION OF VEGETABLES, FLOWERS, RICE, FRUIT, VINES, HOPS OR SEAWEED; FORESTRY; WATERING
    • A01G13/00Protecting plants
    • A01G13/02Protective coverings for plants; Coverings for the ground; Devices for laying-out or removing coverings
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23BPRESERVING, e.g. BY CANNING, MEAT, FISH, EGGS, FRUIT, VEGETABLES, EDIBLE SEEDS; CHEMICAL RIPENING OF FRUIT OR VEGETABLES; THE PRESERVED, RIPENED, OR CANNED PRODUCTS
    • A23B4/00General methods for preserving meat, sausages, fish or fish products
    • A23B4/10Coating with a protective layer; Compositions or apparatus therefor
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23BPRESERVING, e.g. BY CANNING, MEAT, FISH, EGGS, FRUIT, VEGETABLES, EDIBLE SEEDS; CHEMICAL RIPENING OF FRUIT OR VEGETABLES; THE PRESERVED, RIPENED, OR CANNED PRODUCTS
    • A23B5/00Preservation of eggs or egg products
    • A23B5/06Coating eggs with a protective layer; Compositions or apparatus therefor
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23BPRESERVING, e.g. BY CANNING, MEAT, FISH, EGGS, FRUIT, VEGETABLES, EDIBLE SEEDS; CHEMICAL RIPENING OF FRUIT OR VEGETABLES; THE PRESERVED, RIPENED, OR CANNED PRODUCTS
    • A23B7/00Preservation or chemical ripening of fruit or vegetables
    • A23B7/16Coating with a protective layer; Compositions or apparatus therefor
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23BPRESERVING, e.g. BY CANNING, MEAT, FISH, EGGS, FRUIT, VEGETABLES, EDIBLE SEEDS; CHEMICAL RIPENING OF FRUIT OR VEGETABLES; THE PRESERVED, RIPENED, OR CANNED PRODUCTS
    • A23B9/00Preservation of edible seeds, e.g. cereals
    • A23B9/14Coating with a protective layer; Compositions or apparatus therefor
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D5/00Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes

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  • Engineering & Computer Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Zoology (AREA)
  • Food Science & Technology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Environmental Sciences (AREA)
  • Toxicology (AREA)
  • Materials Engineering (AREA)
  • General Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Storage Of Fruits Or Vegetables (AREA)

Abstract

The composition for forming the protective coating may comprise a first group of compounds, wherein each compound of the first group is a fatty acid, fatty acid ester, or fatty acid salt having a carbon chain length of at least 14 carbons. The composition may optionally comprise a second group of compounds selected from fatty acids, fatty acid esters, fatty acid salts, and combinations thereof, wherein each compound of the second group has a carbon chain length of 7 to 13 carbons. At least some of the compounds of the first group may act as emulsifiers, thereby dissolving, suspending or dispersing the composition in a solvent. At least some of the compounds of the second group may act as wetting agents to improve the surface wettability of the article to be coated when a solution, suspension or colloid containing the composition is applied to the article.

Description

Compounds and formulations for protective coatings
Statement of related application
This application claims the benefit of U.S. provisional application 62/727,501 filed on 5.9.2018, U.S. provisional application 62/728,702 filed on 7.9.2018, and U.S. patent application 16/427,219 filed on 30.5.2019, all of which are incorporated herein for all purposes.
FIELD OF THE DISCLOSURE
Described herein are compounds and formulations for forming protective coatings and methods of making and using the same.
Background
Common agricultural products are susceptible to degradation and decomposition (i.e., spoilage) when exposed to the environment. Such agricultural products may include, for example, eggs, fruits, vegetables, agricultural products, seeds, nuts, flowers, and/or whole plants (including processed and semi-processed forms thereof). Edible non-agricultural products (e.g., vitamins, candy, etc.) may also be susceptible to degradation when exposed to the surrounding environment. Degradation of agricultural and other edible products can occur in a non-biological manner due to evaporation of moisture from the outer surface of the product into the atmosphere, diffusion of oxygen oxidation from the environment into the product, mechanical damage to the surface, and/or light-induced degradation (i.e., photodegradation). Biotic stressors (such as bacteria, fungi, viruses and/or pests) may also infect and decompose the product.
The cells that form the aerial surfaces of most plants, such as higher plants, include the outer membrane or epidermis, which provides varying degrees of protection depending on the plant species and plant organs (e.g., fruit, seeds, bark, flowers, leaves, stems, etc.) from water loss, oxidation, mechanical damage, photodegradation, and/or biotic stressors. Cutin is a biopolyester derived from cellular lipids, which constitutes the main structural component of the epidermis and serves to protect plants from environmental (abiotic and biotic) stress sources. The thickness, density and composition of cutin (i.e., the different types of cutin-forming monomers and their relative proportions) may vary depending on the plant species, plant organs within the same or different plant species, and plant maturity stages. The cutin-containing portion of the plant may also contain other compounds (e.g., epidermal waxes, phenolic resins, antioxidants, colored compounds, proteins, polysaccharides, etc.). This difference in the composition of cutin and the thickness and density of the cuticle at different stages of maturation between plant species, plant organs, and/or a given plant can result in plant species or plant organs having varying degrees of resistance to attack by environmental (i.e., water loss, oxidation, mechanical damage, and light) and/or biological (e.g., fungal, bacterial, viral, insect, etc.) stressors.
Conventional methods of preventing degradation, maintaining quality and extending the life of agricultural products include special packaging and/or refrigeration. Refrigeration requires capital intensive equipment, requires constant energy consumption, can result in product damage or degradation if not strictly controlled, must be actively managed, and its benefits are lost when the temperature controlled supply chain is interrupted. The loss of quality of the produce (e.g., water loss) during storage increases humidity, which requires strict maintenance of relative humidity levels (e.g., use of a condenser) to avoid negative effects (e.g., condensation, microbial proliferation, etc.) during storage. In addition, respiration in agricultural products is an exothermic process that releases heat into the surrounding atmosphere. During transport and storage in transport containers, the heat generated by the respiration of agricultural products as well as the external environmental conditions and the heat generated by mechanical processes (e.g., motors) require active cooling of the storage containers in order to maintain a proper storage temperature, which is a major cost driver for the transport companies. By reducing the rate of degradation, reducing heat generation during storage and transportation, and extending the shelf life of agricultural products, there is direct value to key stakeholders throughout the supply chain.
New more cost effective methods are needed to prevent degradation, reduce heat and moisture generation, maintain quality, and extend the life of agricultural products. Such methods may require less or no refrigeration, special packaging, etc.
SUMMARY
Described herein are compositions and formulations for forming protective coatings and methods of making and using the same. The composition may comprise a first group of compounds, wherein each compound of the first group is selected from the group consisting of fatty acids, fatty acid esters, and fatty acid salts, and each compound of the first group has a carbon chain length of at least 14 carbons. The composition may further comprise a second group of compounds selected from the group consisting of fatty acids, fatty acid esters, fatty acid salts, and combinations thereof, wherein each compound of the second group has a carbon chain length of 7 to 13 carbons. At least some of the compounds of the first group (e.g., fatty acid salts) may act as emulsifiers to dissolve, suspend or disperse the composition in the solvent. At least some of the compounds of the second group may act as wetting agents or surfactants to improve the surface wetting of the article to be coated when a solution, suspension or colloid comprising the composition is applied to the article. The fatty acid salt having a carbon chain length of less than 14 (e.g. 7 to 13 carbons) may also (or alternatively) act as an emulsifier, allowing the composition to be dissolved, suspended or dispersed in a solvent.
Thus, in a first aspect, a composition may comprise from about 50% to about 99.9% by mass of one or more first compounds selected from the group consisting of fatty acids, fatty acid esters, fatty acid salts, and combinations thereof, wherein each of the one or more first compounds has a carbon chain length of at least 14. The composition may further comprise about 0.1% to about 35% by mass of one or more second compounds selected from the group consisting of fatty acids, fatty acid esters, fatty acid salts, and combinations thereof, wherein each of the one or more second compounds has a carbon chain length in the range of 7 to 13.
In a second aspect, a composition may comprise from about 50% to about 99.8% by mass of one or more first compounds selected from the group consisting of fatty acids, fatty acid esters, and combinations thereof, wherein each compound of the first group has a carbon chain length of at least 14. The composition may also comprise from about 0.1% to about 35% by mass of one or more humectants. The composition may also comprise from about 0.1% to about 25% by mass of one or more fatty acid salts, wherein each fatty acid salt has a carbon chain length of at least 14.
In a third aspect, a composition may comprise from about 50% to about 99.8% by mass of a first group of compounds, wherein each compound of the first group is a compound of formula I having a carbon chain length of at least 14, and wherein formula I is as defined herein. The composition may further comprise from about 0.1% to about 35% by mass of a second group of compounds, wherein each compound of the second group is a compound of formula I having a carbon chain in the range of 7 to 13. The composition may further comprise from about 0.1% to about 25% by mass of a third group of compounds, wherein each compound of the third group is a salt comprising a compound of formula II. For the first and second groups of compounds, R may be selected from-H, -glyceryl, -C1-C6Alkyl, -C2-C6Alkenyl, -C2-C6Alkynyl, -C3-C7Cycloalkyl, aryl or heteroaryl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl or heteroaryl is optionally substituted by one or more groups selected from halogen, hydroxy, nitro, -CN, -NH2、–SH、–SR15、–OR14、–NR14R15、–C1-C6Alkyl, -C2-C6Alkenyl or-C2-C6Radical substitution of alkynyl. For the third group of compounds, X may be the cationic moiety.
In a fourth aspect, a composition may comprise from about 50% to about 99% by mass of one or more fatty acid esters having a carbon chain length of at least 14 and from about 1% to about 50% by mass of one or more fatty acid salts having a carbon chain length of at least 14.
In a fifth aspect, a composition may comprise (I) 50% to 99% by mass of a first group of compounds, wherein each compound of the first group is a compound of formula I, and (II) 1% to 50% by mass of a second group of compounds, wherein each compound of the second group is a salt of formula II or formula III, wherein formulae I, II and III are as defined herein.
In a sixth aspect, a mixture (e.g., a solution, suspension, or colloid) may comprise a composition in a solvent, wherein the composition comprises (I) 50% to 99% by mass of a first group of compounds, wherein each compound of the first group is a compound of formula I, and (II) 1% to 50% by mass of a second group of compounds, wherein each compound of the second group is a salt of formula II or formula III, wherein formulae I, II and III are as defined herein.
Any composition or mixture described herein can include one or more of the following features, alone or in combination. The second compound or humectant may have a carbon chain length of 8, 10, 11 or 12. Any compound in the composition can be a compound of formula I. The cationic moiety may be an organic or inorganic ion. The cationic portion may include sodium. Each of the one or more second compounds can be a humectant. The one or more first compounds may include monoacylglycerides and/or fatty acid salts. The fatty acid ester may comprise a monoacylglycerol. The mass ratio of fatty acid ester (e.g., monoacylglyceride) to fatty acid salt may be in the range of about 2 to 100 or about 2 to 99. Thus, the mass ratio of the first group of compounds to the second group of compounds may be in the range of 2 to 99 or 2 to 100. The composition may comprise less than 10% by mass of diglycerides. The composition may comprise less than 10% by mass of triglycerides. Each compound of the first and/or second group of compounds may have a carbon chain length of at least 14. In formula I, R may be-glyceryl. The second group of compounds may include SA-Na, PA-Na, MA-Na, SA-K, PA-K, or MA-K. The composition may comprise 70 to 99% by mass of the first group of compounds and 1 to 30% by mass of the second group of compounds. The solvent may be water, or may be at least 50% or at least 70% water by volume. The concentration of the composition in the mixture may range from 0.5 to 200 mg/mL. The first group of compounds may include one or more compounds selected from the group consisting of:
Figure BDA0003045368940000041
Figure BDA0003045368940000051
Figure BDA0003045368940000061
Figure BDA0003045368940000071
Figure BDA0003045368940000081
Figure BDA0003045368940000091
Figure BDA0003045368940000101
Figure BDA0003045368940000111
Figure BDA0003045368940000121
Figure BDA0003045368940000131
Figure BDA0003045368940000141
Figure BDA0003045368940000151
Figure BDA0003045368940000161
Figure BDA0003045368940000171
Figure BDA0003045368940000181
Figure BDA0003045368940000191
in another aspect, a mixture (e.g., a solution, suspension, or colloid) can comprise any of the compositions described herein in a solvent (e.g., dissolved, suspended, or dispersed in a solvent). Any of the blends described herein may include one or more of the following features. The solvent may be characterized as having a contact angle of at least about 70 degrees on carnauba wax. The solvent may be water, or may be at least 70% water by volume. The solvent may include ethanol. The solvent may include water and ethanol. The mixture may include an antimicrobial agent, which may be, for example, citric acid. The concentration of the composition in the mixture may range from 0.5 to 200 mg/mL. The concentration of the humectant in the mixture may be at least about 0.1 mg/mL.
In another aspect, a method of forming a mixture can include providing a solvent characterized by exhibiting a contact angle of at least about 70 ° (e.g., at least about 75 °, at least about 80 °, at least about 85 °, or at least about 90 °) when placed on a surface of carnauba wax. The method may further comprise adding the composition to a solvent to form a mixture. The composition may comprise one or more fatty acids or salts or esters thereof, and/or may comprise a compound of formula I, formula II and/or formula III. The resulting mixture is characterized by exhibiting a contact angle of less than about 85 ° (e.g., less than about 80 °, less than about 75 °, less than about 70 °, or less than about 65 °) when placed on carnauba wax. The contact angle of the resulting mixture on the carnauba wax may be less than the contact angle of the solvent (prior to addition of the composition) on the carnauba wax. Optionally, at least one of the fatty acids or salts or esters thereof of the composition can have a carbon chain length of 13 or less. Optionally, at least one of the fatty acids or salts or esters thereof of the composition can have a carbon chain length of 14 or greater. Optionally, the solvent may be water, or may be at least 70% water by volume.
In another aspect, a method of forming a protective coating on a substrate (e.g., an agricultural product) can include applying a mixture (e.g., a solution, suspension, or colloid) to a surface of the substrate, the mixture including a composition in a solvent. The method may further include removing the solvent from the surface of the substrate, thereby causing the protective coating to be formed from the composition on the surface of the substrate. The composition may include a compound of formula I, formula II, and/or formula III, wherein formulae I, II and III are described throughout. For example, the composition may comprise (I) 50% to 99% by mass of a first group of compounds, wherein each compound of the first group is a compound of formula I, and (II) 1% to 50% by mass of a second group of compounds, wherein each compound of the second group is a salt of formula II or formula III.
Drawings
Figure 1 shows a graph of the daily mass loss rate of finger oranges (finger lime) coated with 1-and 2-glycerides of palmitic acid.
Figure 2 shows a graph of the mass loss factor for avocados coated with a combination of 1-and 2-glycerides of palmitic, stearic and myristic acids.
FIG. 3 shows a graph of the mass loss factor of avocados coated with a combination of fatty acids (MA, PA and SA) and glycerides of fatty acids (MA-1G, PA-1G and SA-1G).
Figure 4 shows a graph of the mass loss factor of avocados coated with a combination of 1-glycerides of palmitic, stearic and myristic acids.
Figure 5 is a high resolution photograph of avocados treated with a mixture of 1-glycerides of undecanoic acid suspended in water.
Fig. 6 is a graph of the percent mass loss of treated and untreated blueberries over a 5 day period.
FIG. 7 shows a graph of the mass loss factor for lemons treated with various concentrations of SA-1G and SA-Na (mass ratio 4:1) suspended in water.
Figure 8 shows a graph of the mass loss factor of lemons treated with a mixture comprising various coating agents suspended in water.
Fig. 9 is a high resolution photograph of avocados treated with a mixture comprising a combination of medium and long chain fatty acid esters/salts suspended in water.
Fig. 10 and 11 show graphs of the contact angle of various mixtures on a non-waxed lemon surface.
Fig. 12 shows a graph of contact angles of various solvents and mixtures on the surface of unsaled lemon, candelilla and carnauba waxes.
Figure 13 shows a graph of the mass loss factor for avocados treated with mixtures comprising various combinations of medium and long chain fatty acid esters/salts suspended in water.
Figure 14 shows a graph of the mass loss factor for cherries treated with mixtures comprising various combinations of medium and long chain fatty acid esters/salts suspended in water.
Figure 15 shows a graph of the average daily mass loss rate for finger oranges treated with mixtures comprising various combinations of medium and long chain fatty acid esters/salts suspended in water.
Fig. 16 shows a graph of the contact angle of various solvents and mixtures on a paraffin surface.
Fig. 17 shows the contact angle of a droplet on a solid surface.
Fig. 18 shows a graph of the average daily mass loss rate of avocados treated with mixtures comprising various combinations of fatty acid esters and fatty acid salts suspended in water.
Figure 19 shows a graph of the average daily mass loss rate of avocados treated with mixtures comprising various combinations of fatty acid esters and emulsifiers suspended in water.
Figure 20 shows a graph of the mass loss factor for avocados treated with mixtures comprising various combinations of fatty acid esters and emulsifiers suspended in water at different concentrations.
Figure 21 shows a graph of the respiratory factor of avocados treated with mixtures comprising various combinations of fatty acid esters and emulsifiers suspended in water at different concentrations.
Fig. 22 shows a representative image of a drop of a mixture comprising a combination of a fatty acid ester and a fatty acid salt on a surface.
Fig. 23 shows a representative image of a droplet of a mixture comprising a combination of fatty acid esters and sodium lauryl sulfate on a surface.
Fig. 24 illustrates a source of heat generation or conduction in a transport container.
Fig. 25 shows the average temperature of the avocado box stack in various orientations, untreated and coated with a mixture of fatty acid esters and fatty acid salts, after removal from the 10 ℃ storage.
Definition of
As used herein, the term "plant matter" refers to any part of a plant, including, for example, fruits (in a botanical sense, including pericarp and juice sacs), vegetables, leaves, stems, bark, seeds, flowers, pericarp, or roots. Plant matter includes pre-harvest plants or parts thereof and post-harvest plants or parts thereof, including, for example, harvested fruits and vegetables, harvested roots and berries, and harvested flowers.
As used herein, "coating agent" refers to a composition comprising a compound or group of compounds that can form a protective coating.
As used herein, the term "contact angle" of a liquid on a solid surface refers to the angle of the outer surface of a drop of liquid measured where the liquid-gas interface meets the liquid-solid interface. For example, as shown in FIG. 17, the angle θCThe contact angle of the droplet 1701 on the surface of the solid 1702 is defined. The contact angle quantifies the wettability of a liquid on a solid surface.
As used herein, the term "wetting agent" or "surfactant" each refers to a compound that, when added to a solvent, suspension, colloid, or solution, reduces the difference in surface energy between the solvent/suspension/colloid/solution and the solid surface on which the solvent/suspension/colloid/solution is placed.
As used herein, the "carbon chain length" of a fatty acid or a salt or ester thereof refers to the number of carbon atoms in the chain including the carbonyl carbons.
As used herein, "long chain fatty acid," "long chain fatty acid ester," or "long chain fatty acid salt" refers to a fatty acid having a carbon chain length greater than 13 (i.e., at least 14), or an ester or salt thereof, respectively.
As used herein, "medium chain fatty acid," "medium chain fatty acid ester," or "medium chain fatty acid salt" refers to fatty acids or esters or salts thereof, respectively, having a carbon chain length in the range of 7 to 13, including 7 and 13.
As used herein, a "cationic counterion" is any organic or inorganic positively charged ion associated with a negatively charged ion. Examples of cationic counterions include, for example, sodium, potassium, calcium, and magnesium.
As used herein, a "cationic moiety" is any organic or inorganic positively charged ion.
The following abbreviations are used throughout. Palmitic acid (i.e., palmitic acid) is abbreviated "PA". Octadecanoic acid (i.e., stearic acid) is abbreviated "SA". Myristic acid (i.e. myristic acid) is abbreviated "MA". (9Z) -Octadecenoic acid (i.e., oleic acid) is abbreviated "OA". Dodecanoic acid (e.g., lauric acid) is abbreviated "LA". Undecanoic acid (e.g., undecanoic acid) is abbreviated "UA". Capric acid (e.g. n-capric acid) is abbreviated "CA". Palmitic acid 1, 3-dihydroxypropan-2-yl ester (i.e., palmitic acid 2-glyceryl ester) is abbreviated as "PA-2G". Octadecanoic acid 1, 3-dihydroxypropan-2-yl ester (i.e., stearic acid 2-glyceryl ester) is abbreviated "SA-2G". 1, 3-dihydroxypropan-2-yltetradecanoic acid (i.e., myristic acid 2-glyceryl ester) is abbreviated "MA-2G". (9Z) -Octadecenoic acid 1, 3-dihydroxypropan-2-yl ester (i.e., oleic acid 2-glyceryl ester) is abbreviated "OA-2G". Palmitic acid 2, 3-dihydroxypropan-1-yl ester (i.e., palmitic acid 1-glyceryl ester) is abbreviated "PA-1G". Octadecanoic acid 2, 3-dihydroxypropan-1-yl ester (i.e., stearic acid 1-glyceryl ester) is abbreviated "SA-1G". Tetradecanoic acid 2, 3-dihydroxypropan-1-yl ester (i.e., myristic acid 1-glyceryl ester) is abbreviated "MA-1G". (9Z) -Octadecenoic acid 2, 3-dihydroxypropan-1-yl ester (i.e., oleic acid 1-glyceryl ester) is abbreviated "OA-1G". Dodecanoic acid 2, 3-dihydroxypropan-1-yl ester (i.e., 1-glyceryl laurate) is abbreviated "LA-1G". 2, 3-Dihydroxypropan-1-yl undecanoate (i.e., 1-glyceryl undecanoate) is abbreviated as "UA-1G'. Capric acid 2, 3-dihydroxypropan-1-yl ester (i.e. 1-glyceryl n-decanoate) is abbreviated "CA-1G". The sodium salt of stearic acid is abbreviated "SA-Na". The sodium salt of myristic acid is abbreviated "MA-Na". The sodium salt of palmitic acid is abbreviated as "PA-Na". The potassium salt of stearic acid is abbreviated "SA-K". The potassium salt of myristic acid is abbreviated "MA-K". The potassium salt of palmitic acid is abbreviated "PA-K". Calcium salt of stearic acid is abbreviated "(SA)2-Ca ". Calcium salt of myristic acid abbreviated "(MA)2-Ca ". Calcium salt of palmitic acid abbreviated as "(PA)2-Ca ". Magnesium salt of stearic acid abbreviated "(SA)2-Mg ". Magnesium salt of myristic acid abbreviated "(MA)2-Mg ". Magnesium salts of palmitic acid are abbreviated as "(PA)2-Mg”。
As used herein, "substituted" or "substituent" means that one atom or group of atoms is replaced with another atom or group of atoms. Exemplary substituents include, but are not limited to, halogen, hydroxy, nitro, cyano, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, formyl, acyl, ether, ester, keto, aryl, heteroaryl, and the like.
As used herein, "mass loss rate" refers to the rate at which a product loses mass (e.g., by releasing water and other volatile compounds). The mass loss rate is typically expressed as a raw mass percentage per unit time (e.g., per day).
As used herein, the term "quality loss factor" is defined as the ratio of the average mass loss rate of uncoated produce (measured against a control) to the average mass loss rate of the corresponding coated produce at a given time. Thus, a greater mass loss factor corresponds to a greater reduction in the average mass loss rate of the coated produce.
As used herein, "respiration rate" refers to the CO release from a product2And more particularly the CO released per unit mass of product per unit time2Volume (at standard temperature and pressure). The respiration rate is usually expressed as ml CO2Kg.h. The respiration rate of the product can be measured by the following procedure: placing the product in a container equipped with CO2In a closed container of known volume for the sensorRecording CO in the container2The change in concentration with time, and then the CO required to obtain the measured concentration value is calculated2The release rate.
As used herein, the term "respiration factor" is defined as the ratio of the cumulative respiration of an uncoated agricultural product (measured against a control group) to the cumulative respiration of the corresponding coated agricultural product. Thus, a greater respiration factor corresponds to a greater reduction in cumulative respiration of the coated agricultural product.
Detailed Description
Described herein are solutions, suspensions, or colloids comprising compositions (e.g., coating agents) in solvents that can be used to form protective coatings on substrates such as plant matter, agricultural products, or food products. The protective coating may, for example, prevent moisture loss from the substrate, oxidize the substrate, and/or may protect the substrate from threats such as bacteria, fungi, viruses, and the like. The coating may also protect the substrate from physical damage (e.g., scratches) and photo damage. Thus, the coating agents, solutions/suspensions/colloids, and coatings formed therefrom, can be used to help store agricultural products or other food products for extended periods of time without deterioration. In some cases, the coatings and coating agents that form them can keep food fresh without refrigeration. The coatings and coatings described herein may also be edible (i.e., the coatings and coatings may be non-toxic for human consumption). In some embodiments, the solution/suspension/colloid includes a wetting agent or surfactant that allows the solution/suspension/colloid to better spread across the entire surface of the substrate during application, thereby improving the surface coverage and overall performance of the resulting coating. In some embodiments, the solution/suspension/colloid includes an emulsifier that improves the solubility of the coating agent in the solvent and/or suspends or disperses the coating agent in the solvent. The wetting agent and/or emulsifier may each be a component of the coating agent or may be added separately to the solution/suspension/colloid.
Plant matter (e.g., agricultural products) and other degradable items can be protected from degradation by biotic or abiotic stress sources by forming a protective coating on the outer surface of the product. Can be achieved in the following mannerForming a coating: the ingredients of the coating (collectively referred to herein as "coating agents") are added to a solvent (e.g., water and/or ethanol) to form a mixture (e.g., a solution, suspension, or colloid), the mixture is applied to the exterior surface of the product, for example, by dipping the product to be coated into the mixture or by spraying the mixture onto the surface of the product, and then the solvent is removed from the surface of the product, for example, by allowing the solvent to evaporate, such that the coating is formed from the coating agent on the surface of the product. The coating agent may be formulated such that the resulting coating provides a barrier to water and/or oxygen transfer, thereby preventing water loss and/or oxidation of the coated product. The coating agent may additionally or alternatively be formulated such that the resulting coating provides protection against CO2A barrier to ethylene and/or other gas transfer.
Coating agents that include long chain fatty acids (e.g., palmitic acid, stearic acid, myristic acid, and/or other fatty acids having a carbon chain length greater than 13) and/or esters or salts thereof can be both safe for human consumption and can be used as coating agents to form coatings that are effective in reducing mass loss and oxidation in various products. For example, it has been shown that coatings formed from coating agents comprising palmitic acid, myristic acid, stearic acid, 1-glyceride of palmitic acid (i.e., 2, 3-dihydroxypropan-1-yl palmitate, herein "PA-1G"), 2-glyceride of palmitic acid (i.e., 1, 3-dihydroxypropan-2-yl palmitate, herein "PA-2G"), 1-glyceride of myristic acid (i.e., 2, 3-dihydroxypropan-1-yl myristate, herein "MA-1G"), 1-glyceride of stearic acid (i.e., 2, 3-dihydroxypropan-1-yl stearate, herein "SA-1G"), and/or various combinations of other long chain fatty acids or salts or esters thereof are effective in reducing many types of agricultural products (e.g., orange, brown sugar, or salts or esters thereof), Avocado, blueberry, and lemon). Specific examples of various coatings and their effect on reducing the rate of mass loss in various types of agricultural products are provided in examples 1-4 below.
Medium chain fatty acids (e.g., with carbon chain lengths in the range of 7 to 13) and/or salts or esters thereof may also be used as coating agents to form coatings on agricultural or other plant matter or agricultural products using the methods described above. However, it has generally been found that these compounds cause damage to agricultural or plant matter and also generally result in minimal or no reduction in the rate of mass loss. For example, it was shown that treatment of avocados with a solution of 1-glyceride undecanoate (i.e., 2, 3-dihydroxypropan-1-yl undecanoate, herein "UA-1G") (the carbon chain length of UA-1G is 11) suspended in water at a concentration as low as 5mg/mL can result in the skin of the avocado changing from an almost completely green color to a high density black color-changing region due to damage to the skin by UA-1G. As shown in fig. 5, which is a high resolution photograph of one of the avocados 500 treated with the suspension described above, the skin of the previously green avocado after treatment exhibits a number of black discolored areas 502.
It is generally desirable for a coating formulated to prevent moisture loss or oxidation of a coated substrate (such as agricultural produce) that a thicker coating is less permeable to water and oxygen than a thinner coating formed from the same coating agent, and therefore should have a lower rate of mass loss than a thinner coating. Thicker coatings can be formed by increasing the concentration of the coating agent in the solution/suspension/colloid and applying a similar volume of solution/suspension/colloid to each (similarly sized) agricultural product. The effect of increasing the coating thickness on harvested produce is demonstrated in fig. 6, which shows a graph of the percent mass loss over 5 days for untreated blueberries (602), blueberries treated with a first solution comprising 10mg/mL of a coating compound dissolved in ethanol (604), and blueberries treated with a second solution comprising 20mg/mL of a coating compound dissolved in ethanol (606). The coating agents in the first and second solutions were each about 75% PA-2G and about 25% PA-1G by mass. As shown, the mass loss rate of the blueberries decreased significantly with increasing coating thickness.
For certain solutions/suspensions/colloids comprising long chain fatty acids and/or salts or esters thereof dissolved or suspended or dispersed in a solvent, it was found that a protective coating formed by the above method on certain types of agricultural products can reduce the rate of quality loss of the agricultural products, but as the thickness of the coating increases, the rate of quality loss does not decrease, as in the above-described blueberries. In contrast, the mass loss rate in these cases was found to be lower than that of the uncoated agricultural product, but was about the same for thinner and thicker coatings. For example, FIG. 7 shows a graph of the mass loss factor for lemons treated with various concentrations of coating agents (e.g., SA-1G and SA-Na combined at a mass ratio of 4:1) suspended or dispersed in water. Bar 702 corresponds to a group of untreated lemons. Bar 704 corresponds to a group of lemons having a concentration of 10mg/mL coating agent in solvent. Bar 706 corresponds to a group of lemons having a concentration of 20mg/mL coating agent in solvent. Bar 708 corresponds to a group of lemons having a concentration of coating agent in solvent of 30 mg/mL. Bar 710 corresponds to a set of lemons having a concentration of 40mg/mL coating agent in solvent. The bars 712 correspond to a group of lemons having a concentration of coating agent in solvent of 50 mg/mL. As shown in fig. 7, although the mass loss factor was greater than 1 for all coated lemons (indicating that the coating reduced the mass loss rate), the mass loss rate was about the same for all coating agent concentrations tested in the range of 10mg/mL to 50mg/mL and therefore did not vary with concentration.
Surprisingly, for many cases (as in the case of the lemon in fig. 7) where the mass loss rate does not vary with the coating thickness, it was found that if low concentrations of medium chain fatty acids and/or salts or esters thereof are added to the mixture prior to application to the agricultural products (e.g., by including them in the coating agent at a lower concentration than long chain fatty acids and/or salts or esters thereof, or by adding them separately to the mixture), the mass loss rate does increase with the coating thickness. Furthermore, in many of these cases, the resulting rate of mass loss of the coating comprising a low concentration of medium chain fatty acids and/or salts or esters thereof is significantly lower, but otherwise the same, than the coating formed from a coating agent lacking medium chain fatty acids and/or salts or esters thereof, in which case there is no or little surface damage to the agricultural product. These results are particularly surprising in view of the fact that medium chain fatty acids and/or salts or esters thereof are commonly found to cause damage to agricultural products or other plant matter when administered alone at similar concentrations, as shown in figure 5.
The beneficial effect of adding a low concentration of medium chain fatty acids or salts or esters thereof to a coating solution/suspension/colloid comprising long chain fatty acids or salts/esters thereof is shown in fig. 8. Figure 8 is a graph showing untreated lemons (802), lemons treated with a suspension in which the coating agent includes only long chain fatty acid esters and fatty acid salts (804 and 806), and lemons treated with a suspension in which the coating agent includes a low concentration of medium chain fatty acids or salts or esters thereof and a high concentration of long chain fatty acid esters and fatty acid salts (808 and 810). Specifically, bar 804 corresponds to lemons treated with 10mg/mL long chain fatty acid ester/salt suspended in water. Bar 806 corresponds to lemon treated with 30mg/mL long chain fatty acid ester/salt solvent in water. Bar 808 corresponds to lemons treated with 10mg/mL long chain fatty acid ester/salt plus 5mg/mL medium chain fatty acid ester solvent in water. Bar 810 corresponds to lemons treated with 30mg/mL long chain fatty acid ester/salt plus 5mg/mL medium chain fatty acid ester solvent in water.
While treatment of lemons (804 and 806) with coating agents comprising only long chain fatty acid salts and esters did reduce the average mass loss rate of lemons, the mass loss factor did not increase significantly when the concentration of the coating compound in the mixture was increased from 10mg/mL (804) to 30mg/mL (806). However, the mass loss factor did increase significantly when low concentrations of medium chain fatty acid esters (5mg/mL UA-1G) were added to each mixture. Specifically, the addition of 5mg/mL medium chain ester with 10mg/mL long chain fatty acid ester/salt to the mixture increased the mass loss factor of the lemon from about 1.5 (bar 804) to about 1.9 (bar 808) due to the resulting coating, corresponding to an increase in mass loss factor of over 25%. The addition of 5mg/mL medium chain ester with 30mg/mL long chain fatty acid ester/salt to the mixture increased the mass loss factor of the lemon from about 1.7 (bar 806) to about 2.6 (bar 810) due to the resulting coating, corresponding to an increase in mass loss factor of over 50%. The mass loss factor of the lemons corresponding to bar 810 is in fact significantly greater than that of the group of lemons coated with any concentration of long chain fatty acid esters/salts without the addition of medium chain fatty acids or salts/esters thereof in solution.
Figure 9 is a high resolution photograph of avocados 900 treated with the same mixture of lemons (5mg/mL UA-1G plus 30mg/mL long chain fatty acid esters/salts suspended in water) as used in treatment bar 810 of figure 8. Prior to treatment, the avocado skin was almost completely green (not shown). As shown in fig. 9, after the treatment, the avocado epidermis remained mostly green with only a small density of black discolored areas 902, indicating that the treatment had little damage to the avocado epidermis. In contrast, the avocados shown in figure 5 (treated with a solution comprising the same concentration of UA-1G (5mg/mL) in water but lacking long chain fatty acid esters/salts) showed extensive skin damage.
Without wishing to be bound by theory, it is believed that many mixtures (i.e., solutions, suspensions, or colloids) lacking medium chain fatty acids or salts/esters thereof do not adequately wet the entire surface of the agricultural product to which they are applied due to the different surface energies of the mixtures as compared to the surface of the agricultural product. Thus, the coatings formed from these mixtures do not completely cover the surface of the agricultural product. Thus, the mass loss is primarily the loss of water through the openings in the coating and is relatively unaffected by increasing the thickness of the coating. Thus, where such an effect is believed to occur (e.g., in a lemon coated with a water-based solution such as in fig. 7), the rate of mass loss is relatively unaffected by increasing the coating thickness.
It is further believed that the medium chain fatty acids added to the mixture act as surfactants/wetting agents, thereby reducing the contact angle of the mixture on the surface of the agricultural product. It is believed that the addition of the humectant improves the coverage of the mixture on the surface of the agricultural product, allowing a substantially continuous coating to be formed over the entire surface. Thus, the rate of mass loss of the coated produce was found to decrease with increasing coating thickness, and the overall rate of mass loss was found to be significantly lower than that of produce coated with a similar mixture lacking the wetting agent. Furthermore, the long chain fatty acids and/or salts or esters thereof appear to inhibit the surface damage to agricultural products observed with wetting agents dissolved, dispersed or suspended in a mixture and applied alone when long chain fatty acids and/or salts or esters thereof are not included. Additional evidence of these effects is provided below.
Through extensive experimentation, it was found that droplets of some solvents and coating solutions/suspensions had relatively large contact angles on at least some types of agricultural product surfaces, indicating that the droplets had very different surface energies than the agricultural product surfaces. This effect is particularly pronounced where the coating solution/suspension is at least 70% water by volume, as the surface of many plants or other agricultural products tends to be hydrophobic due to the presence of epidermal wax. This phenomenon is characterized as follows. Droplets of solvent or coating solution/suspension/colloid (i.e., solvent in which the coating agent is dissolved, suspended or dispersed) are deposited directly on the surface of the agricultural product or directly on carnauba wax, candelilla wax or paraffin wax (all tend to have natural hydrophobicity similar to that of the surface of lemon and many other types of agricultural products, see, e.g., fig. 12), and the contact angle is determined with image analysis software. The results of the various studies are summarized below.
Increasing the concentration of a wetting agent (e.g., a medium chain fatty acid and/or a salt or ester thereof) in a water-based or high water content coating mixture generally reduces the contact angle of the solution/suspension/colloid on the surface of the agricultural product or wax. For example, as shown in fig. 10, water (bar 1002) exhibited a contact angle of about 88 ° on an unsaled lemon surface, and a coating mixture (bar 1004) comprising only long chain fatty acid esters/salts (SA-1G and MA-Na combined at a mass ratio of 95: 5) suspended in water at a concentration of 30mg/mL exhibited a contact angle of about 84 °. However, due to the addition of low concentrations of medium chain fatty acid esters (e.g., CA-1G), the contact angle gradually decreased from about 70 ° for 0.1mg/mL CA-1G (bar 1006) to about 47 ° for 6mg/mL CA-1G (bar 1016).
It has further been found that for many mixtures, the addition of medium chain fatty acids and/or salts or esters thereof having a smaller chain length results in a greater reduction in the contact angle of the droplet on the agricultural product than the addition of a similar concentration of medium chain fatty acids and/or salts or esters thereof having a longer chain length. For example, fig. 11 shows the results of a study in which different medium chain fatty acid esters (C10, C11, and C12) were added to a water-based coating mixture and the contact angles of the droplets of each mixture were measured on non-waxed lemons. The strip 1102 corresponds to a drop of water. Bar 1104 corresponds to SA-1G and MA-Na combined in a mass ratio of 95:5 and suspended in water at a concentration of 30 mg/mL. Bars 1106, 1108 and 1110 correspond to the same mixture as bar 1104, but with 4mg/mL LA-1G (for bar 1106), 4mg/mL UA-1G (for bar 1108) or 4mg/mL CA-1G (for bar 1110) added.
As shown in fig. 11, water droplets (1102) on the lemons and mixtures (1104) containing only long chain fatty acid esters/salts on the lemons showed larger contact angles than the addition of small concentrations of medium chain fatty acid esters (1106, 1108 and 1110). Furthermore, for a given concentration of medium chain fatty acid ester, the contact angle decreases as the carbon chain length decreases. Specifically, the mixture lacking the medium chain fatty acid esters (1102 and 1104) exhibits a contact angle of about 84 ° to 88 °. The addition of 4mg/mL LA-1G (carbon chain length 12) reduced the contact angle to about 67 °, the addition of 4mg/mL UA-1G (carbon chain length 11) reduced the contact angle to about 56 °, and the addition of 4mg/mL CA-1G (carbon chain length 10) reduced the contact angle to about 50 °.
As previously mentioned, carnauba wax, candelilla wax, or paraffin wax were found to have natural hydrophobicity similar to that of the surface of lemon (and other agricultural products). Thus, the wetting properties (e.g., contact angle) of a mixture characterized on the surface of carnauba, candelilla, or paraffin wax can generally be predictive of the wetting properties of the mixture on the produce. For example, FIG. 12 shows the contact angles of water and two other mixtures on the surfaces of lemon (bar 1201-1203), candelilla wax (bar 1211-1213), and carnauba wax (bar 1221-1223). The first set of strips (1201, 1211 and 1221) each corresponds to water, and the contact angles on all 3 surfaces are in the range of about 92 ° to 105 °. The second set of bars (1202, 1212 and 1222) corresponded to a suspension where the solvent was water and the coating agent included 30mg/mL of SA-1G and SA-Na (long chain fatty acid salt) combined in a mass ratio of 94:6, and 0.25mg/mL of citric acid and 0.325mg/mL of sodium bicarbonate. As shown, the contact angle on all 3 surfaces is in the range of about 80 ° to 88 °, which is slightly lower than pure water, but still typically quite large. The third set of bars (1203, 1213 and 1223) corresponds to the same suspension as the second set of bars, but also includes 3mg/mL CA-1G (medium chain fatty acid ester). As shown, the contact angles on all 3 surfaces are still very similar to each other and are greatly reduced, each in the range of about 31 ° to 44 °, compared to the solution lacking the medium chain fatty acid ester.
The effect of adding low concentrations of LA-1G and CA-1G to the coating mixture used to form the coating on avocados is shown in the graph of FIG. 13. As shown, avocados coated with a mixture comprising SA-1G and MA-Na (long chain fatty acid ester/salt) combined in a mass ratio of 94:6 and suspended in water at a concentration of 30mg/mL (bar 1302) exhibited a mass loss factor of about 1.78. Bars 1303-.
Addition of CA-1G (carbon chain length 10) to the coating mixture increased the mass loss factor to about 2.35 at a CA-1G concentration of 1mg/mL (bar 1303), to about 2.24 at a CA-1G concentration of 2.5mg/mL (bar 1304), and to about 2.18 at a CA-1G concentration of 4mg/mL (bar 1305). Thus, while the mass loss factor is significantly greater for all concentrations of CA-1G in the range of 1 to 4mg/mL as compared to the mixture lacking medium chain fatty acid esters (bar 1302), the mass loss factor appears to decrease slightly as the concentration of CA-1G increases. Without wishing to be bound by theory, it is believed that the addition of CA-1G at all concentrations of at least 1mg/mL is effective in improving the wettability of the solution on the avocado surface, but increasing the concentration of CA-1G begins to cause some moderate damage to the avocado, thereby reducing the beneficial surface wetting effect and resulting in a slight reduction in the mass loss factor.
Still referring to FIG. 13, the addition of LA-1G (carbon chain length 12) to the coating mixture reduced the mass loss factor to about 1.61 at LA-1G concentrations of 1mg/mL (bar 1313), but increased the mass loss factor to about 2.15 at LA-1G concentrations of 2.5mg/mL (bar 1314) and 4mg/mL (bar 1315). Without wishing to be bound by theory, it is believed that at a concentration of LA-1G of 1mg/mL, the surface wettability of the solution is not sufficiently improved to overcome the surface damage caused to avocados by LA-1G, and therefore the mass loss factor is reduced relative to treatment by a coating mixture lacking medium chain fatty acid esters. However, for larger concentrations of LA-1G, the surface wettability was sufficiently improved such that the mass loss factor was significantly increased relative to treatment by a coating solution lacking the medium chain fatty acid ester. This result is consistent with the results of FIG. 11, which found that shorter chain fatty esters (e.g., CA-1G) gave a greater reduction in contact angle than longer chain fatty esters (e.g., LA-1G) when added to a water-based coating mixture at the same concentration.
The effect of adding a low concentration of CA-1G to the coating mixture used to form the coating on the cherries is shown in FIG. 14. As shown, cherries coated with a mixture comprising SA-1G and MA-Na (long chain fatty acid ester/salt) combined in a mass ratio of 94:6 and suspended in water at a concentration of 40mg/mL (bar 1402) exhibited a mass loss factor of about 1.60. Bars 1403-1405 show the effect of adding CA-1G to the mixture at concentrations of 0.5mg/mL, 1mg/mL, and 3mg/mL, respectively. Addition of CA-1G (carbon chain length of 10) to the coating mixture increased the mass loss factor to about 1.75 at a CA-1G concentration of 0.5mg/mL (bar 1403), to about 1.96 at a CA-1G concentration of 1mg/mL (bar 1404), and to about 2.00 at a CA-1G concentration of 4mg/mL (bar 1405). As shown, the addition of low concentrations of CA-1G to the mixture increased the mass loss factor of the coated cherries. This increase is believed to result from the addition of CA-1G to the coating mixture improving surface wetting.
The effect of adding a low concentration of UA-1G to the coating mixture used to form the coating on finger orange is shown in fig. 15. As shown, finger oranges coated with a mixture comprising SA-1G and SA-Na (long chain fatty acid ester/salt) combined in a mass ratio of 94:6 and suspended in water at a concentration of 30mg/mL (bar 1502) exhibited a mass loss factor of about 1.61. Bar 1503, 1505 shows the effect of adding UA-1G to a mixture at concentrations of 1mg/mL, 3mg/mL, and 5mg/mL, respectively. Addition of UA-1G (carbon chain length 11) to the mixture increased the mass loss factor to about 2.33 at a UA-1G concentration of 1mg/mL (bar 1503), to about 2.06 at a UA-1G concentration of 3mg/mL (bar 1504), and to about 1.93 at a UA-1G concentration of 5mg/mL (bar 1505). While the addition of UA-1G at all concentrations of 1 to 5mg/mL did increase the orange-directed mass loss factor, the peak mass loss factor occurred at 1mg/mL and the mass loss factor decreased as the concentration of UA-1G increased. Without wishing to be bound by theory, it is believed that increasing the concentration of UA-1G begins to damage the surface of the orange, and any improvement in surface wettability due to increased concentration of UA-1G is insufficient to mitigate this effect, thus resulting in a gradual decrease in the mass loss factor with increasing concentration of UA-1G.
As described throughout, a wetting agent may be included in the coating solution/suspension/colloid in order to improve the surface wettability of the substrate to which the solution/suspension/colloid is applied, thereby improving the surface coverage of the coating formed thereon. The wetting agent may be included within or as part of a coating agent dissolved or suspended in a solvent to form a coating solution/suspension/colloid. That is, the subset of compounds of the coating agent may cause a change in the surface energy of the solvent to which the coating agent is added, thereby acting as a wetting agent. Alternatively, the wetting agent may be a compound (or group of compounds) separate from the coating agent and may be added to the solvent before, after, or simultaneously with the coating agent.
Alternatively, the wetting agent may be a compound (or group of compounds) separate from the coating agent and may be applied to the surface prior to application of the coating agent. For example, the humectant may first be added to a separate solvent to form a humectant solution/suspension/colloid. The wetting agent solution/suspension/colloid may then be applied to the surface, and then the coating solution/suspension/colloid is applied to the surface to form the coating. Priming the surface in this manner improves the surface wetting of the coating solution/suspension/colloid with the surface.
An example of the above surface priming effect is shown in fig. 16, which is a graph of the contact angle of various solvents or mixtures on a paraffin surface. As shown, water applied directly to the paraffin surface (bar 1601) exhibited an average contact angle of 74 °. When a coating agent mixture of SA-1G and SA-Na combined at a mass ratio of 95:5 was dispersed in water at a concentration of 45mg/mL and applied directly onto the paraffin surface (bar 1602), the average contact angle was even greater (83 °). However, when a wetting agent (e.g., a medium chain fatty acid or salt/ester thereof) is added to the coating agent mixture, the contact angle of the coating agent mixture is significantly reduced. Alternatively, when a wetting agent (e.g. a medium chain fatty acid or salt/ester thereof) is applied to the paraffin surface prior to the application of the water or coating agent mixture, the contact angle is also significantly reduced. For example, when 3mg/mL CA-1G was added to the mixture corresponding to bar 1602, the resulting contact angle (bar 1603) was 43 °. When the paraffin surface was primed by applying a wetting agent mixture of CA-1G in water at a concentration of 3mg/mL followed by drying the surface before applying water (bar 1604) or applying the SA-1G/SA-Na coating agent mixture described above (bar 1605), the resulting contact angles were 24 ° and 30 °, respectively.
The solvent to which the coating agent and wetting agent (when separate from the coating agent) are added to form a solution/suspension/colloid may be, for example, water, methanol, ethanol, isopropanol, butanol, acetone, ethyl acetate, chloroform, acetonitrile, tetrahydrofuran, diethyl ether, methyl tert-butyl ether, alcohol, any other suitable solvent, or a combination thereof. The resulting solution, suspension or colloid may be suitable for forming a coating on an agricultural product. For example, a solution, suspension, or colloid can be applied to the surface of the agricultural product, and then the solvent can be removed (e.g., by evaporation or convection drying), leaving a protective coating formed from the coating agent on the surface of the agricultural product.
While the various solvents described above (particularly water and ethanol) may be safely and effectively used in solutions/suspensions/colloids applied to edible products such as agricultural or other agricultural products, in many cases it may be advantageous to use at least about 40% (and in many cases more) water or other solvent by volume. This is because water is generally less expensive than other suitable solvents and is also safer than solvents that are more volatile and/or have a lower flash point (e.g., acetone or an alcohol such as isopropanol or ethanol). Thus, for any solution/suspension/colloid described herein, the solvent or solution/suspension/colloid may be at least about 40%, at least about 45%, at least about 50%, at least about 55%, at least about 60%, at least about 65%, at least about 70%, at least about 75%, at least about 80%, at least about 85%, at least about 90%, at least about 95%, or at least about 99% water by mass or by volume. In some embodiments, the solvent comprises a combination of water and ethanol, and optionally may be at least about 40%, at least about 45%, at least about 50%, at least about 55%, at least about 60%, at least about 65%, at least about 70%, at least about 75%, at least about 80%, at least about 85%, at least about 90%, at least about 95%, or at least about 99% water by volume. In some embodiments, the solvent or solution/suspension/colloid may be about 40% to 100% water by mass or volume, about 40% to 99% water by mass or volume, about 40% to 95% water by mass or volume, about 40% to 90% water by mass or volume, about 40% to 85% water by mass or volume, about 40% to 80% water by mass or volume, about 50% to 100% water by mass or volume, about 50% to 99% water by mass or volume, about 50% to 95% water by mass or volume, about 50% to 90% water by mass or volume, about 50% to 85% water by mass or volume, about 50% to 80% water by mass or volume, about 60% to 100% water by mass or volume, about 60% to 99% water by mass or volume, about 95% water by mass or volume, about 60% to 99% water by mass or volume, about 95% water by mass or volume, or about 95% water by mass or volume, About 60% to 90% by mass or volume of water, about 60% to 85% by mass or volume of water, about 60% to 80% by mass or volume of water, about 70% to 100% by mass or volume of water, about 70% to 99% by mass or volume of water, about 70% to 95% by mass or volume of water, about 70% to 90% by mass or volume of water, about 70% to 85% by mass or volume of water, about 80% to 100% by mass or volume of water, about 80% to 99% by mass or volume of water, about 80% to 97% by mass or volume of water, about 80% to 95% by mass or volume of water, about 80% to 93% by mass or volume of water, about 80% to 90% by mass or volume of water, about 85% to 100% by mass or volume of water, about 85% to 85% by volume of water, about 85% by mass or volume of water, About 85 to 95% water by mass or volume, about 90 to 100% water by mass or volume, about 90 to 99% water by mass or volume, about 90 to 98% water by mass or volume, or about 90 to 97% water by mass or volume.
In view of the above, for some applications, the solvent may be a low wettability solvent (i.e., a solvent that exhibits a large contact angle with respect to the surface to which it is applied). For example, the contact angle between a solvent and (a) carnauba wax, (b) candelilla wax, (c) paraffin wax, or (d) an unsaled lemon surface may be at least about 70 °, such as at least about 75 °,80 °, 85 °, or 90 °, in the absence of any added wetting agent or other surfactant. The addition of any wetting agent described herein to a solvent, alone or in combination with other compounds or coating agents, can result in a contact angle between the resulting solution/suspension/colloid and (a) carnauba wax, (b) candelilla wax, (c) paraffin wax, or (d) an unwashed lemon surface of less than about 85 °, e.g., less than about 80 °, 75 °,70 °, 65 °,60 °, 55 °,50 °, 45 °,40 °, 35 °,30 °, 25 °,20 °, 15 °,10 °,5 °, or 0 °.
The coating agent added to the solvent or dissolved, suspended or dispersed in the solvent to form a coating solution/suspension/colloid can be any compound or combination of compounds capable of forming a protective coating on the substrate to which the solution/suspension/colloid is applied. The coating agent may be formulated such that the resulting coating protects the substrate from biotic and/or abiotic stress sources. For example, the coating may prevent or inhibit the transfer of oxygen and/or water, thereby preventing oxidation of the substrate and/or loss of moisture through transpiration/permeation/evaporation. In the case where the substrate is perishable and/or edible, for example when the substrate is a plant, agricultural product or agricultural produce, the coating agent preferably consists of a non-toxic compound that is safe for consumption. For example, the coating agent may be formed from or include a fatty acid and/or a salt or ester thereof. The fatty acid ester may be, for example, an ethyl ester, a methyl ester or a glyceride (e.g., a 1-glyceride or a 2-glyceride).
It has been found that coating agents formed from or comprising a high percentage of long chain fatty acids and/or salts or esters thereof (e.g., having a carbon chain length of at least 14) are effective in forming protective coatings on various substrates that prevent water loss and/or oxidation of the substrate. The addition of one or more medium chain fatty acids and/or salts or esters thereof (or other wetting agents) may further improve the performance of the coating. Thus, the coating agents herein may comprise one or more compounds of formula I, wherein formula I is:
Figure BDA0003045368940000321
wherein:
r is selected from-H, -glyceryl, -C1-C6Alkyl, -C2-C6Alkenyl, -C2-C6Alkynyl, -C3-C7Cycloalkyl, aryl or heteroaryl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl or heteroaryl is optionally substituted with one or more substituents selected from halogen (e.g., Cl, Br or I), hydroxy, nitro, -CN, -NH2、-SH、-SR15、-OR14、-NR14R15、C1-C6Alkyl radical, C2-C6Alkenyl or C2-C6Radical substitution of alkynyl;
R1、R2、R5、R6、R9、R10、R11、R12and R13Each occurrence of the formula is independently-H, - (C ═ O) R14、–(C=O)H、–(C=O)OH、–(C=O)OR14、–(C=O)-O-(C=O)R14、–O(C=O)R14、–OR14、–NR14R15、–SR14Halogen, -C1-C6Alkyl, -C2-C6Alkenyl, -C2-C6Alkynyl, -C3-C7Cycloalkyl, aryl OR heteroaryl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl OR heteroaryl is optionally substituted by one OR more-OR14、–NR14R15、–SR14Or halogen substitution;
R3、R4、R7and R8At each occurrence independently is-H, -OR14、–NR14R15、–SR14Halogen, -C1-C6Alkyl, -C2-C6Alkenyl, -C2-C6Alkynyl, -C3-C7CycloalkanesOR aryl OR heteroaryl, wherein each alkyl, alkynyl, cycloalkyl, aryl OR heteroaryl is optionally substituted by one OR more-OR14、–NR14R15、–SR14Or halogen substitution; or
R3And R4May combine with the carbon atom to which they are attached to form C3-C6Cycloalkyl radical, C4-C6Cycloalkenyl or 3 to 6 membered ring heterocycle; and/or
R7And R8May combine with the carbon atom to which they are attached to form C3-C6Cycloalkyl radical, C4-C6Cycloalkenyl or 3 to 6 membered ring heterocycle;
R14and R15Each occurrence independently is-H, aryl, heteroaryl, -C1-C6Alkyl, -C2-C6Alkenyl or-C2-C6An alkynyl group;
(symbol)
Figure BDA0003045368940000331
represents a single bond or a cis-or trans-double bond;
n is 0, 1,2, 3, 4, 5, 6, 7 or 8;
m is 0, 1,2 or 3;
q is 0, 1,2, 3, 4 or 5; and is
r is 0, 1,2, 3, 4, 5, 6, 7 or 8.
In some embodiments, R is selected from-H, -CH3or-CH2CH3. In some embodiments, R is selected from-H, -glyceryl, -C1-C6Alkyl, -C2-C6Alkenyl, -C2-C6Alkynyl, -C3-C7Cycloalkyl, aryl or heteroaryl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl or heteroaryl is optionally substituted by one or more C1-C6Alkyl or hydroxy substituted.
As further described herein, the coating agent can additionally or alternatively include a fatty acid salt, such as a sodium salt (e.g., SA-Na, PA-N)a or MA-Na), potassium salts (e.g. SA-K, PA-K, MA-K), calcium salts (e.g. (SA)2-Ca、(PA)2-Ca or (MA)2Ca) or magnesium salts (e.g. (SA)2-Mg、(PA)2-Mg or (MA)2-Mg). Thus, the coating agents herein may comprise one or more compounds of formula II or formula III, wherein formula II and formula III are:
Figure BDA0003045368940000341
wherein, for each formula:
x is a cation part;
Xp+is a cationic counterion having a charge state p, and p is 1,2 or 3;
R1、R2、R5、R6、R9、R10、R11、R12and R13Each occurrence of the formula is independently-H, - (C ═ O) R14、–(C=O)H、–(C=O)OH、–(C=O)OR14、–(C=O)-O-(C=O)R14、–O(C=O)R14、–OR14、–NR14R15、–SR14Halogen, -C1-C6Alkyl, -C2-C6Alkenyl, -C2-C6Alkynyl, -C3-C7Cycloalkyl, aryl OR heteroaryl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl OR heteroaryl is optionally substituted by one OR more-OR14、–NR14R15、–SR14Or halogen substitution;
R3、R4、R7and R8At each occurrence independently is-H, -OR14、–NR14R15、–SR14Halogen, -C1-C6Alkyl, -C2-C6Alkenyl, -C2-C6Alkynyl, -C3-C7Cycloalkyl, aryl or heteroaryl, wherein each alkyl, alkynyl, cycloalkyl, aryl or heteroaryl is optionally substitutedBy one OR more-OR14、–NR14R15、–SR14Or halogen substitution; or
R3And R4May combine with the carbon atom to which they are attached to form C3-C6Cycloalkyl radical, C4-C6Cycloalkenyl or 3 to 6 membered ring heterocycle; and/or
R7And R8May combine with the carbon atom to which they are attached to form C3-C6Cycloalkyl radical, C4-C6Cycloalkenyl or 3 to 6 membered ring heterocycle;
R14and R15Each occurrence independently is-H, aryl, heteroaryl, -C1-C6Alkyl, -C2-C6Alkenyl or-C2-C6An alkynyl group;
(symbol)
Figure BDA0003045368940000342
represents a single bond or a cis-or trans-double bond;
n is 0, 1,2, 3, 4, 5, 6, 7 or 8;
m is 0, 1,2 or 3;
q is 0, 1,2, 3, 4 or 5; and is
r is 0, 1,2, 3, 4, 5, 6, 7 or 8.
Any of the coating agents described herein can include one or more of the following medium chain fatty acid compounds (e.g., compounds of formula I):
Figure BDA0003045368940000351
Figure BDA0003045368940000352
or
Figure BDA0003045368940000353
Any of the coating agents described herein can include one or more of the following long chain fatty acid compounds (e.g., compounds of formula I):
Figure BDA0003045368940000354
Figure BDA0003045368940000361
Figure BDA0003045368940000371
Figure BDA0003045368940000381
or
Figure BDA0003045368940000382
The coating agents herein can include one or more of the following medium chain fatty acid methyl ester compounds (e.g., compounds of formula I):
Figure BDA0003045368940000383
Figure BDA0003045368940000384
or
Figure BDA0003045368940000385
The coating agents herein may include one or more of the following long chain fatty acid methyl ester compounds (e.g., compounds of formula I):
Figure BDA0003045368940000386
Figure BDA0003045368940000391
Figure BDA0003045368940000401
Figure BDA0003045368940000411
Figure BDA0003045368940000412
or
Figure BDA0003045368940000413
The coating agents herein may include one or more of the following medium chain fatty acid ethyl ester compounds (e.g., compounds of formula I):
Figure BDA0003045368940000414
Figure BDA0003045368940000415
or
Figure BDA0003045368940000416
The coating agents herein may include one or more of the following long chain fatty acid ethyl ester compounds (e.g., compounds of formula I):
Figure BDA0003045368940000417
Figure BDA0003045368940000421
Figure BDA0003045368940000431
Figure BDA0003045368940000441
Figure BDA0003045368940000442
or
Figure BDA0003045368940000443
The coating agents herein may include one or more of the following medium chain fatty acid 2-glyceride compounds (e.g., compounds of formula I):
Figure BDA0003045368940000444
Figure BDA0003045368940000445
or
Figure BDA0003045368940000451
The coating agents herein may include one or more of the following long chain fatty acid 2-glyceride compounds (e.g., compounds of formula I):
Figure BDA0003045368940000452
Figure BDA0003045368940000461
Figure BDA0003045368940000471
Figure BDA0003045368940000481
or
Figure BDA0003045368940000482
The coating agents herein may include one or more of the following medium chain fatty acid 1-glyceride compounds (e.g., compounds of formula I):
Figure BDA0003045368940000483
Figure BDA0003045368940000484
or
Figure BDA0003045368940000485
The coating agents herein may include one or more of the following long chain fatty acid 1-glyceride compounds (e.g., compounds of formula I):
Figure BDA0003045368940000491
Figure BDA0003045368940000501
Figure BDA0003045368940000511
Figure BDA0003045368940000521
Figure BDA0003045368940000531
Figure BDA0003045368940000532
or
Figure BDA0003045368940000533
The coating agents herein may include one or more of the following fatty acid salts (e.g., compounds of formula II or formula III), wherein X is a cationic counterion and n represents the charge state (i.e., proton equivalent charge number):
Figure BDA0003045368940000541
Figure BDA0003045368940000551
Figure BDA0003045368940000561
Figure BDA0003045368940000571
Figure BDA0003045368940000572
or
Figure BDA0003045368940000573
In some embodiments, n is 1,2, or 3. In some embodiments, X is sodium, potassium, calcium, or magnesium.
As previously mentioned, it has been shown that coating agents formed primarily of various combinations of compounds of formula I having carbon chain lengths of at least 14 each (e.g., at least 50% by mass or by molar composition of coating agents of compounds of formula I) can form protective coatings on agricultural and other agricultural products that can be effective in reducing moisture loss and oxidation. As previously mentioned, the coating may be formed on the outer surface of the agricultural product by: dissolving, suspending or dispersing the coating agent in a solvent to form a mixture, applying the mixture to the surface of the agricultural product (e.g., by spraying the coating onto the product, by dipping the product into the mixture, or by brushing the mixture onto the surface of the product), and then removing the solvent (e.g., by allowing the solvent to evaporate). The solvent may include any polar, non-polar, protic or aprotic solvent, including any combination thereof. Examples of solvents that may be used include water, methanol, ethanol, isopropanol, butanol, acetone, ethyl acetate, chloroform, acetonitrile, tetrahydrofuran, diethyl ether, methyl tert-butyl ether, any other suitable solvent, or a combination thereof. In the case of applying the coating to a plant or other edible product, it may be preferable to use an edible safe solvent, such as water, ethanol, or a combination thereof. Depending on the solvent used, the solubility limit of the coating agent in the solvent may be below the limit required for a particular application. For example, when a compound of formula I is used as a coating agent and the solvent is water (or primarily water), the solubility limit of the coating agent may be relatively low. In these cases, it is still possible to add the desired concentration of coating agent to the solvent and form a suspension or colloid.
The coating agent may further include an emulsifier in order to improve the solubility of the coating agent in the solvent or to suspend or disperse the coating agent in the solvent. When a coating is to be formed on a plant or other edible product, it may be preferred that the emulsifier be safe to eat. Furthermore, it is also preferred not to incorporate an emulsifier into the coating or if an emulsifier is incorporated into the coating, it does not reduce the properties of the coating.
Through extensive experimentation, it has been shown that an organic salt (e.g., a compound of formula II or formula III) added to a coating agent can increase the solubility of the coating agent or suspend or disperse the coating agent in a solvent having a substantial water content (e.g., a solvent of at least 50% water by volume), provided that the concentration of the salt cannot be too low (relative to the concentration of the compound of formula I). Furthermore, the added salt does not substantially degrade the properties of the subsequently formed coating, provided that the concentration of the salt (relative to the concentration of the compound of formula I) is not too high.
For example, a coating agent comprising a first set of compounds of formula I mixed with a second set of compounds of formula II and/or III may be added to water to form a suspension by: the water is heated to about 70 ℃, the coating agent is added, and the resulting mixture is then cooled to about room temperature (or lower). The cooled mixture can then be applied to a substrate (such as agricultural produce) to form a protective coating, as described herein. However, it has been found that when the compound of formula I comprises at least 50% by mass of the coating agent and the compound of formula II and/or III comprises less than about 3% by mass of the coating agent, the coating agent cannot be suspended in water at elevated temperature, or the coating agent can be suspended in water at higher temperature but fall out with decreasing temperature, thereby preventing the formation of a coating from the mixture.
In addition, if the concentration of the compounds of formula II and/or III is too high, the properties of the resulting coating may be reduced. For example, as shown in FIG. 18 and example 13 below, a 94:6 mixture of a compound of formula I (PA-1G and SA-1G) and a compound of formula II or III (SA-Na) formed a coating on avocado that resulted in a mass loss factor of 1.88. However, when repeated studies were performed with a 70:30 mixture of the same compounds, the mass loss factor for coated avocados was reduced to 1.59. As further shown in fig. 18, when the compound of formula II or III in the coating agent is MA-Na, a similar decrease in the mass loss factor is observed at high salt concentrations in the coating agent.
In view of the above, a composition (e.g., a coating agent) can include a first group of compounds comprising one or more compounds of formula I (e.g., fatty acids or esters thereof) and a second group of compounds comprising one or more salts of formula II or formula III (e.g., fatty acid salts). The compound of formula I and/or the salt of formula II or III may optionally have a carbon chain length of at least 14. The mass ratio of the first group of compounds (e.g. compounds of formula I, such as fatty acids or esters, including monoacylglycerides) to the second group of compounds (salts, e.g. fatty acid salts, of formula II or III) may, for example, be in the range of about 2 to 200, such as about 2 to 100, 2 to 99, 2 to 90, 2 to 80, 2 to 70, 2 to 60, 2 to 50, 2 to 40, 2 to 30, 2 to 25, 2 to 20, 2 to 15, 2 to 10, 2.5 to 200, 2.5 to 100, 2.5 to 90, 2.5 to 80, 2.5 to 70, 2.5 to 60, 2.5 to 50, 2.5 to 40, 2.5 to 30, 2.5 to 25, 2.5 to 20, 2.5 to 15, 2.5 to 10, 3 to 200, 3 to 100, 3 to 90, 3 to 80, 3 to 70, 3 to 60, 3 to 50, 3 to 40, 3 to 30, 3 to 20, 3 to 15, 4 to 4, 4 to 50, 4 to 4, 4 to 50, 4 to 80, 4 to 40, 4 to 30, 4 to 25, 4 to 20, 4 to 15, 4 to 10, 5 to 200, 5 to 100, 5 to 90, 5 to 80, 5 to 70, 5 to 60, 5 to 50, 5 to 40, 5 to 30, 5 to 25, 5 to 20, 5 to 15, 5 to 10, 10 to 100, 10 to 99, 10 to 90, 10 to 80, 10 to 70, 10 to 60, 10 to 50, 10 to 40, 10 to 30, 10 to 25, 10 to 20, 10 to 15, 15 to 100, 15 to 99, 15 to 90, 15 to 80, 15 to 70, 15 to 60, 15 to 50, 15 to 40, 15 to 30, 15 to 25, or 15 to 20.
As mentioned above, the coating agent may be added or dissolved, suspended or dispersed in a solvent to form a colloid, suspension or solution. The various components of the coating agent (e.g., the compound of formula I and the salt) can be combined prior to addition to the solvent and then added together to the solvent. Alternatively, the components of the coating agent may be kept separate from each other and then added to the solvent sequentially (or at separate times).
The concentration of the first group of compounds (compounds of formula I) in the solvent/solution/suspension/colloid may, for example, be in the range of from about 1mg/mL to about 200mg/mL, such as from about 1 to 150mg/mL, from 1 to 100mg/mL, from 1 to 90mg/mL, from 1 to 80mg/mL, from 1 to 75mg/mL, from 1 to 70mg/mL, from 1 to 65mg/mL, from 1 to 60mg/mL, from 1 to 55mg/mL, from 1 to 50mg/mL, from 1 to 45mg/mL, from 1 to 40mg/mL, from 2 to 200mg/mL, from 2 to 150mg/mL, from 2 to 100mg/mL, from 2 to 90mg/mL, from 2 to 80mg/mL, from 2 to 75mg/mL, from 2 to 70mg/mL, from 2 to 65mg/mL, from 2 to 60mg/mL, from 2 to 55mg/mL, or from, 2 to 50mg/mL, 2 to 45mg/mL, 2 to 40mg/mL, 5 to 200mg/mL, 5 to 150mg/mL, 5 to 100mg/mL, 5 to 90mg/mL, 5 to 80mg/mL, 5 to 75mg/mL, 5 to 70mg/mL, 5 to 65mg/mL, 5 to 60mg/mL, 5 to 55mg/mL, 5 to 50mg/mL, 5 to 45mg/mL, 5 to 40mg/mL, 10 to 200mg/mL, 10 to 150mg/mL, 10 to 100mg/mL, 10 to 90mg/mL, 10 to 80mg/mL, 10 to 75mg/mL, 10 to 70mg/mL, 10 to 65mg/mL, 10 to 60mg/mL, 10 to 55mg/mL, 10 to 50mg/mL, 10 to 45mg/mL, or 10 to 40 mg/mL.
The concentration of the second group of compounds (salts of formula II or formula III, e.g. fatty acid salts) in the solvent/solution/suspension/colloid may, for example, be in the range of from about 0.01mg/mL to about 80mg/mL, such as from about 0.01 to 75mg/mL, 0.01 to 70mg/mL, 0.01 to 65mg/mL, 0.01 to 60mg/mL, 0.01 to 55mg/mL, 0.01 to 50mg/mL, 0.01 to 45mg/mL, 0.01 to 40mg/mL, 0.01 to 35mg/mL, 0.01 to 30mg/mL, 0.01 to 25mg/mL, 0.01 to 20mg/mL, 0.01 to 15mg/mL, 0.01 to 10mg/mL, 0.1 to 80mg/mL, 0.1 to 75mg/mL, 0.1 to 70mg/mL, 0.1 to 65mg/mL, 0.1 to 60mg/mL, 0.1 to 55mg/mL, 0.1 to 50mg/mL, 0.1 to 45mg/mL, 0.1 to 40mg/mL, 0.1 to 35mg/mL, 0.1 to 30mg/mL, 0.1 to 25mg/mL, 0.1 to 20mg/mL, 0.1 to 15mg/mL, 0.1 to 10mg/mL, 1 to 80mg/mL, 1 to 75mg/mL, 1 to 70mg/mL, 1 to 65mg/mL, 1 to 60mg/mL, 1 to 55mg/mL, 1 to 50mg/mL, 1 to 45mg/mL, 1 to 40mg/mL, 1 to 35mg/mL, 1 to 30mg/mL, 1 to 25mg/mL, 1 to 20mg/mL, 1 to 15mg/mL, 1 to 10mg/mL, 2 to 80mg/mL, 2 to 75mg/mL, 2 to 70mg/mL, 2 to 65mg/mL, 2 to 60mg/mL, 2 to 55mg/mL, 2 to 50mg/mL, 2 to 45mg/mL, 2 to 40mg/mL, 2 to 35mg/mL, 2 to 30mg/mL, 2 to 25mg/mL, 2 to 20mg/mL, 2 to 15mg/mL, or 2 to 10 mg/mL.
The concentration of the composition (e.g., coating agent) in the solvent/solution/suspension/colloid can, for example, be in the range of about 1mg/mL to about 200mg/mL, such as about 1 to 150mg/mL, 1 to 100mg/mL, 1 to 90mg/mL, 1 to 80mg/mL, 1 to 75mg/mL, 1 to 70mg/mL, 1 to 65mg/mL, 1 to 60mg/mL, 1 to 55mg/mL, 1 to 50mg/mL, 1 to 45mg/mL, 1 to 40mg/mL, 2 to 200mg/mL, 2 to 150mg/mL, 2 to 100mg/mL, 2 to 90mg/mL, 2 to 80mg/mL, 2 to 75mg/mL, 2 to 70mg/mL, 2 to 65mg/mL, 2 to 60mg/mL, 2 to 55mg/mL, 2 to 50mg/mL, 2 to 45mg/mL, 2 to 40mg/mL, 5 to 200mg/mL, 5 to 150mg/mL, 5 to 100mg/mL, 5 to 90mg/mL, 5 to 80mg/mL, 5 to 75mg/mL, 5 to 70mg/mL, 5 to 65mg/mL, 5 to 60mg/mL, 5 to 55mg/mL, 5 to 50mg/mL, 5 to 45mg/mL, 5 to 40mg/mL, 10 to 200mg/mL, 10 to 150mg/mL, 10 to 100mg/mL, 10 to 90mg/mL, 10 to 80mg/mL, 10 to 75mg/mL, 10 to 70mg/mL, 10 to 65mg/mL, 10 to 60mg/mL, 10 to 55mg/mL, 10 to 50mg/mL, 10 to 45mg/mL, or 10 to 40 mg/mL.
As also described above and demonstrated in the examples below, the coating solution/suspension/colloid may also include a wetting agent to reduce the contact angle between the solution/suspension/colloid and the substrate surface being coated. The wetting agent may be included as a component of the coating agent and thus added to the solvent at the same time as the other components of the coating agent. Alternatively, the wetting agent may be separate from the coating agent and may be added to the solvent before, after, or simultaneously with the coating agent. Alternatively, the wetting agent may be separate from the coating agent and may be applied to the surface prior to the coating agent to prime the surface.
The humectant may be a fatty acid or a salt or ester thereof. The humectant may be a compound or group of compounds of formula I, II or III, wherein formulae I, II and III are given above. In particular, the humectant compounds may each have a carbon chain length of 13 or less. For example, the carbon chain length may be 7, 8, 9, 10, 11, 12, 13 in the range of 7 to 13 or in the range of 8 to 12. The humectant may also or alternatively be one or more of a phospholipid, a lysophospholipid, a glycoglycerolipid, a glycolipid, an ascorbate ester of a fatty acid, an ester of lactic acid, an ester of tartaric acid, an ester of malic acid, an ester of fumaric acid, an ester of succinic acid, an ester of citric acid, an ester of pantothenic acid, or a fatty alcohol derivative (e.g. an alkyl sulfate). In some embodiments, the humectants included in the mixtures herein are edible and/or safe to eat.
The contact angle between the solvent/solution/suspension/colloid and the carnauba, candelilla, or paraffin wax may be at least about 70 °, such as at least about 75 °, at least about 80 °, at least about 85 °, or at least about 90 °, before the humectant is added to the solvent (and before or after the coating agent is added, for the case where the humectant and coating agent are separate). After addition of the wetting agent to the solvent (and before or after addition of the coating agent for the case where the wetting agent and coating agent are separate), the contact angle between the resulting solution/suspension/colloid and carnauba wax, candelilla wax, or paraffin wax may be less than 85 °, e.g., less than about 80 °, less than about 75 °, less than about 70 °, less than about 65 °, less than about 60 °, less than about 55 °, less than about 50 °, less than about 45 °, less than about 40 °, less than about 35 °, less than about 30 °, less than about 25 °, less than about 20 °, less than about 15 °, less than about 10 °, less than about 5 °, or about 0 °.
Since the wetting agent may in many cases damage the substrate to be coated, the concentration of the wetting agent compound may be less than the concentration of the other components of the coating agent. However, if the concentration of the wetting agent added to the solvent is too low, the surface energy of the resulting solution/suspension/colloid may not be substantially different from the surface energy of the solvent, in which case improved surface wettability of the substrate may not be achieved.
In some embodiments, the compound that acts as a wetting agent may also (or alternatively) act as an emulsifier. For example, in some embodiments, a medium chain fatty acid (e.g., with a carbon chain length of 7, 8, 9, 10, 11, 12, or 13) or a salt or ester thereof is used as an emulsifier (and optionally also acts as a wetting agent) in the composition, thereby enabling the composition to be dissolved or suspended in a solvent. In some embodiments, a phospholipid, lysophospholipid, glycoglycerolipid, glycolipid, ascorbate ester of a fatty acid, ester of lactic acid, ester of tartaric acid, ester of malic acid, ester of fumaric acid, ester of succinic acid, ester of citric acid, ester of pantothenic acid, or fatty alcohol derivative (e.g., alkyl sulfate) is included in the composition and functions as an emulsifier (and optionally also functions as a humectant). In some embodiments, the emulsifier is cationic. In some embodiments, the emulsifier is anionic. In some embodiments, the emulsifier is zwitterionic. In some embodiments, the emulsifier is uncharged.
In view of the above, any of the compositions (e.g., coating agents) described herein can include a first set of compounds of formula I, II and/or III (e.g., fatty acids and/or salts or esters thereof) and a second set of compounds of formula I, II and/or III (e.g., fatty acids and/or salts or esters thereof), wherein each compound of the first set of compounds has a carbon chain length of at least 14 and each compound of the second set of compounds has a carbon chain length of 13 or less (e.g., in the range of 7 to 13). The first and second groups of compounds can each include, for example, an ethyl ester, a methyl ester, a glycerol ester (e.g., a monoacylglycerol ester, such as a 1-monoacylglycerol or a 2-monoacylglycerol ester), a sodium salt of a fatty acid, a potassium salt of a fatty acid, a calcium salt of a fatty acid, a magnesium salt of a fatty acid, or a combination thereof. In some embodiments, any of the compositions described herein can include a first set of compounds of formula I (e.g., fatty acids and/or esters thereof) and a second set of compounds, wherein the second set of compounds functions as an emulsifier (e.g., is a fatty acid salt, a phospholipid, a lysophospholipid, a glycoglycerolipid, a glycolipid, an ascorbate ester of a fatty acid, an ester of lactic acid, an ester of tartaric acid, an ester of malic acid, an ester of fumaric acid, an ester of succinic acid, an ester of citric acid, an ester of pantothenic acid, or a fatty alcohol derivative (e.g., an alkyl sulfate)).
The mass ratio of fatty acids and/or esters in the first set of compounds to emulsifiers in the second set of compounds can be within any of the ranges given previously (e.g., ranges such that the solubility of the coating agent in the solvent is sufficient to dissolve, suspend, or disperse the desired concentration of coating agent in the solvent). The mass ratio of the first group of compounds (carbon chain length of at least 14) to the second group of compounds (carbon chain length of 13 or less, or emulsifier) may be in the range of about 2 to 200, for example about 2 to 100, 2 to 90, 2 to 80, 2 to 70, 2 to 60, 2 to 50, 2 to 40, 2 to 30, 2 to 25, 2 to 20, 2 to 15, 2 to 10, 2.5 to 200, 2.5 to 100, 2.5 to 90, 2.5 to 80, 2.5 to 70, 2.5 to 60, 2.5 to 50, 2.5 to 40, 2.5 to 30, 2.5 to 25, 2.5 to 20, 2.5 to 15, 2.5 to 10, 3 to 200, 3 to 100, 3 to 90, 3 to 80, 3 to 70, 3 to 60, 3 to 50, 3 to 40, 3 to 30, 3 to 25, 3 to 20, 3 to 15, 3 to 10, 3 to 200, 3 to 100, 3 to 90, 3 to 80, 4 to 4, 4 to 20, 4 to 4, 4 to 20, 4 to 4, 4 to 20, 4 to 30, 4 to 20, 4 to, 4 to 10, 5 to 200, 5 to 100, 5 to 90, 5 to 80, 5 to 70, 5 to 60, 5 to 50, 5 to 40, 5 to 30, 5 to 25, 5 to 20, 5 to 15, or 5 to 10.
As shown in fig. 19, a mixture comprising a fatty acid ester (e.g., monoacylglyceride) and various emulsifiers can be used as a coating on agricultural products (e.g., fresh produce) to reduce the rate of quality loss. For example, as shown in FIG. 19 and example 14 below, a 94:6 mixture of compounds of formula I (PA-1G and SA-1G) and compounds of formula II or III (SA-Na) formed a coating on avocado with a mass loss rate of 0.84% per day (bar 1902). The coating formed on avocado from a 94:6 mixture of compounds of formula I (PA-1G and SA-1G) and a fatty alcohol derivative (e.g., sodium lauryl sulfate) resulted in a mass loss rate of 0.69 per day (bar 1903). The coating formed on avocado from a 70:30 mixture of compounds of formula I (PA-1G and SA-1G) and a phospholipid (e.g., lecithin) resulted in a mass loss rate of 1.08% per day (bar 1904). All exemplified blends resulted in a reduction in the mass loss rate of avocados compared to untreated controls, which had a mass loss rate of 1.44% per day (bar 1901).
As shown in fig. 20 and 21, the concentrations of fatty acid esters (e.g., monoacylglycerides) and emulsifiers may affect the mass loss factor and respiratory factor of avocados. For example, as shown in FIG. 20, increasing the concentration of a 94:6 mixture of compounds of formula I (PA-1G and SA-1G) and compounds of formula II or III (SA-Na) from 20G/L (bar 2001) to 30G/L (bar 2003) increased the mass loss factor from 1.57 to 1.64. Increasing the concentration from 30g/L (bar 2003) to 40g/L (bar 2005) increased the mass loss factor from 1.64 to 1.81. Accordingly, as shown in FIG. 21, the respiratory factor also increased from 1.21 at 20g/L (bar 2101) to 1.22 at 30g/L (bar 2103) to 1.31 at 40g/L (bar 2105). A concentration dependence of a 94:6 mixture of the compounds of formula I (PA-1G and SA-1G) with fatty alcohol derivatives (e.g. sodium lauryl sulfate) was also observed. As shown in FIG. 20, the mass loss factor increased from 1.63 at 20g/L (bar 2002) to 1.76 at 30g/L (bar 2004) to 1.88 at 40g/L (bar 2006). Accordingly, as shown in FIG. 21, the respiratory factor also increased from 1.20 at 20g/L (bar 2102) to 1.34 at 30g/L (bar 2104) to 1.41 at 40g/L (bar 2106).
As shown in FIG. 22, a 94:6 mixture of the compounds of formula I (PA-1G and SA-1G) and the compounds of formula II or III (SA-Na) has a contact angle of 95. + -. 5 ℃ at 45G/L. As shown in FIG. 23, the 94:6 mixture of the compounds of formula I (PA-1G and SA-1G) with a fatty alcohol derivative (e.g., sodium lauryl sulfate) had a contact angle of 84. + -. 4 ℃ at 45G/L. Without wishing to be bound by theory, the increase in mass loss factor when using fatty alcohol derivatives (e.g. alkyl sulfates) as emulsifiers may be attributed to improved wettability compared to compounds of formula II or III (SA-Na).
As mentioned above, the coating agent may be added or dissolved, suspended or dispersed in a solvent to form a suspension, colloid or solution. The various components of the coating agent (e.g., the compound of formula I, the salt of formula II and/or III, and/or the wetting agent) can be combined prior to addition to the solvent and then added together to the solvent. Alternatively, at least some components of the coating agent may be kept separate from other components, and may be added to the solvent sequentially (or at separate times).
The concentration of the first group of compounds (compounds of formula I, II and/or III with a carbon chain length of at least 14) in the solvent/solution/suspension/colloid may, for example, be in the range of about 1mg/mL to about 200mg/mL, such as about 1 to 150mg/mL, 1 to 100mg/mL, 1 to 90mg/mL, 1 to 80mg/mL, 1 to 75mg/mL, 1 to 70mg/mL, 1 to 65mg/mL, 1 to 60mg/mL, 1 to 55mg/mL, 1 to 50mg/mL, 1 to 45mg/mL, 1 to 40mg/mL, 2 to 200mg/mL, 2 to 150mg/mL, 2 to 100mg/mL, 2 to 90mg/mL, 2 to 80mg/mL, 2 to 75mg/mL, 2 to 70mg/mL, 2 to 65mg/mL, 2 to 60mg/mL, 2 to 55mg/mL, 2 to 50mg/mL, 2 to 45mg/mL, 2 to 40mg/mL, 5 to 200mg/mL, 5 to 150mg/mL, 5 to 100mg/mL, 5 to 90mg/mL, 5 to 80mg/mL, 5 to 75mg/mL, 5 to 70mg/mL, 5 to 65mg/mL, 5 to 60mg/mL, 5 to 55mg/mL, 5 to 50mg/mL, 5 to 45mg/mL, 5 to 40mg/mL, 10 to 200mg/mL, 10 to 150mg/mL, 10 to 100mg/mL, 10 to 90mg/mL, 10 to 80mg/mL, 10 to 75mg/mL, 10 to 70mg/mL, 10 to 65mg/mL, 10 to 60mg/mL, 10 to 55mg/mL, 10 to 50mg/mL, 10 to 45mg/mL or 10 to 40 mg/mL.
The concentration of the wetting agent or the second group of compounds of formula I, II and/or III (e.g., the compound of formula I and/or the salt of formula II and/or III with a carbon chain length of 13 or less) in the solvent/solution/suspension/colloid can be, for example, from about 0.01mg/mL to about 20mg/mL, such as from about 0.01mg/mL to 15mg/mL, 0.01mg/mL to 12mg/mL, 0.01mg/mL to 10mg/mL, 0.01mg/mL to 9mg/mL, 0.01mg/mL to 8mg/mL, 0.01mg/mL to 7mg/mL, 0.01mg/mL to 6mg/mL, 0.01mg/mL to 5mg/mL, 0.1mg/mL to 20mg/mL, 0.1mg/mL to 15mg/mL, 0.1mg/mL to 12mg/mL, 0.1mg/mL to 10mg/mL, 0.1 to 9mg/mL, 0.1 to 8mg/mL, 0.1 to 7mg/mL, 0.1 to 6mg/mL, 0.1 to 5mg/mL, 0.5 to 20mg/mL, 0.5 to 15mg/mL, 0.5 to 12mg/mL, 0.5 to 10mg/mL, 0.5 to 9mg/mL, 0.5 to 8mg/mL, 0.5 to 7mg/mL, 0.5 to 6mg/mL, or 0.5 to 5 mg/mL.
The composition (e.g., coating agent) added to the solvent may be from about 50% to about 99.9% (e.g., about 60% -99.9%, 65% -99.9%, 70% -99.9%, 75% -99.9%, 80% -99.9%, 85% -99.9%, 90% -99.9%, 50% -99%, 60% -99%, 65% -99%, 70% -99%, 75% -99%, 80% -99%, 85% -99%, 90% -99%, 50% -98%, 60% -98%, 65% -98%, 70% -98%, 75% -98%, 80% -98%, 85% -98%, 90% -98%, 50% -96%, 60% -96%, 65% -96%, 70% -96%, 75% -96% by mass, 80% -96%, 85% -96%, 90% -96%, 50% -94%, 60% -94%, 65% -94%, 70% -94%, 75% -94%, 80% -94%, 85% -94%, or 90% -94%) of a first group of compounds, fatty acids, fatty acid esters, fatty acid salts, or combinations thereof (e.g., a compound of formula I and/or a salt of formula II or formula III), wherein optionally each compound of the first group has a carbon chain length of at least 14. In some embodiments, the first group of compounds are fatty acid esters, such as monoacylglycerides.
The composition added to the solvent (e.g., coating agent) may be from about 0.1% to about 50% (e.g., about 0.1% -45%, 0.1% -40%, 0.1% -35%, 0.1% -30%, 0.1% -25%, 0.1% -20%, 0.1% -15%, 0.1% -10%, 0.1% -8%, 0.1% -6%, 0.1% -5%, 0.1% -4%, 0.4% -50%, 0.4% -45%, 0.4% -40%, 0.4% -35%, 0.4% -30%, 0.4% -25%, 0.4% -20%, 0.4% -15%, 0.4% -10%, 0.4% -8%, 0.4% -6%, 0.4% -5%, 0.4% -4%, 0.7% -50%, 0.7% -45%, 0.7% -40% by mass, 0.7% -35%, 0.7% -30%, 0.7% -25%, 0.7% -20%, 0.7% -15%, 0.7% -10%, 0.7% -8%, 0.7% -6%, 0.7% -5%, 0.7% -4%, 1% -50%, 1% -45%, 1% -40%, 1% -35%, 1% -30%, 1% -25%, 1% -20%, 1% -15%, 1% -10%, 1% -8%, 1% -6%, 1% -5% or 1% -4%) of a second group of compounds, fatty acids, fatty acid esters, fatty acid salts or combinations thereof (e.g., a compound of formula I and/or a salt of formula II and/or III), wherein each compound of the second group optionally has a carbon chain length of 13 or less (e.g., a carbon chain length in the range of 7 to 13). The second group of compounds may act as humectants, as previously described.
The composition added to the solvent (e.g., coating agent) may be from about 0.1% to about 50% (e.g., about 0.1% -45%, 0.1% -40%, 0.1% -35%, 0.1% -30%, 0.1% -25%, 0.1% -20%, 0.1% -15%, 0.1% -10%, 0.1% -8%, 0.1% -6%, 0.1% -5%, 0.1% -4%, 0.4% -50%, 0.4% -45%, 0.4% -40%, 0.4% -35%, 0.4% -30%, 0.4% -25%, 0.4% -20%, 0.4% -15%, 0.4% -10%, 0.4% -8%, 0.4% -6%, 0.4% -5%, 0.4% -4%, 0.7% -50%, 0.7% -45%, 0.7% -40% by mass, 0.7% -35%, 0.7% -30%, 0.7% -25%, 0.7% -20%, 0.7% -15%, 0.7% -10%, 0.7% -8%, 0.7% -6%, 0.7% -5%, 0.7% -4%, 1% -50%, 1% -45%, 1% -40%, 1% -35%, 1% -30%, 1% -25%, 1% -20%, 1% -15%, 1% -10%, 1% -8%, 1% -6%, 1% -5% or 1% -4%) of a third group of compounds, which is composed of salts or fatty acid salts of compounds of formula II or formula III. Each compound of the third group may optionally have a carbon chain length greater than 13. The third group of compounds may act as emulsifiers and, for example, increase the solubility of the coating agent, as previously described.
Any of the coating solutions/suspensions/colloids described herein may also comprise an antimicrobial agent, such as ethanol or citric acid. In some embodiments, the antimicrobial agent is part or a component of the solvent. Any of the coating solutions described herein may also contain other components or additives, such as sodium bicarbonate.
In some embodiments, the coating formed on the agricultural product by the coating agents described herein can be configured to alter the surface energy of the agricultural product. Various properties of the coating can be adjusted by adjusting the crosslink density of the coating described herein, its thickness, or its chemical composition. This can be used, for example, to control ripening of post-harvest fruit or produce. For example, a coating formed from a coating agent comprising predominantly difunctional or multifunctional monomer units may have a higher crosslink density than a coating agent comprising monofunctional monomer units, for example. Thus, coatings formed from di-or multi-functional monomer units may, in some cases, slow the rate of maturation compared to coatings formed from mono-functional monomer units.
In some embodiments, one or more wetting agents (such as those described above) are used to improve the wettability of the surface to which the coating solution/suspension/colloid is applied, but wetting agents are not included in the coating solution/suspension/colloid. Instead, the wetting agent is added to a second solvent (which may be the same or different than the solvent to which the coating agent is added) to form a second mixture, and the second mixture is applied to the surface to be coated before the coating solution/suspension/colloid is applied to the surface. In this case, the second mixture may prime the surface to be coated such that the coating solution/suspension/colloid has a contact angle with the surface that is less than it would otherwise have, thereby improving surface wettability.
Any of the coating agents described herein can also include additional materials that are also transported to the surface with the coating, or deposited separately and then encapsulated by the coating (e.g., the coating is formed at least partially around the additional materials), or deposited separately and then supported by the coating (e.g., the additional materials are anchored to the outer surface of the coating). Examples of such additional materials may include cells, biological signaling molecules, vitamins, minerals, pigments, fragrances, enzymes, catalysts, antifungal agents, antimicrobial agents, and/or slow release drugs. The additional material may be non-reactive with the surface and/or coating of the coated product, or alternatively may be reactive with the surface and/or coating.
In some embodiments, the coating may include an additive configured to, for example, alter the viscosity, vapor pressure, surface tension, or solubility of the coating. The additives may, for example, be configured to increase the chemical stability of the coating. For example, the additive may be an antioxidant configured to inhibit oxidation of the coating. In some embodiments, the additive can reduce or increase the melting temperature or glass transition temperature of the coating. In some embodiments, the additive is configured to reduce water vapor, oxygen, CO2Or the diffusion of ethylene through the coating, or to enable the coating to absorb more Ultraviolet (UV) light, for example, to protect agricultural products (or any other product described herein). In some embodiments, the additive can be configured to provide an intentional scent, such as a scent (e.g., a scent of flowers, fruits, plants, freshness, scent, etc.). In some embodiments, the additives may be configured to provide color and may include, for example, dyes or U.S. Food and Drug Administration (FDA) approved color additives.
Any of the coating agents described herein or coatings formed therefrom can be odorless or have a high flavor threshold, e.g., above 500ppm, and can be odorless or have a high odor threshold. In some embodiments, the material included in any of the coatings described herein can be substantially transparent. For example, the coating agent, solvent, and/or any other additives included in the coating may be selected such that they have substantially the same or similar refractive indices. By matching their refractive indices, they can be optically matched to reduce light scattering and improve light transmission. For example, by utilizing materials having similar refractive indices and having clear, transparent properties, a coating having substantially transparent properties can be formed.
The compositions (e.g., coating agents) described herein can be of high purity. For example, the composition may be substantially free (e.g., containing less than 10% by mass, less than 9% by mass, less than 8% by mass, less than 7% by mass, less than 6% by mass, or less than 5%, 4%, 3%, 2%, or 1% by mass) of diglycerides, triglycerides, acetylated monoglycerides, proteins, polysaccharides, phenols, lignans, aromatic acids, terpenes, flavonoids, carotenoids, alkaloids, alcohols, alkanes, and/or aldehydes. In some embodiments, the composition comprises less than 10% (e.g., less than 9%, 8%, 7%, 6%, 5%, 4%, 3%, 2%, or 1%) by mass of diglycerides. In some embodiments, the composition comprises less than 10% (e.g., less than 9%, 8%, 7%, 6%, 5%, 4%, 3%, 2%, or 1%) by mass of triglycerides. In some embodiments, the composition comprises less than 10% (e.g., less than 9%, 8%, 7%, 6%, 5%, 4%, 3%, 2%, or 1%) by mass of acetylated monoglycerides.
Any of the coatings described herein can be placed on the outer surface of an agricultural product or other substrate using any suitable means. For example, the substrate may be dip coated in a coating formulation bath (e.g., an aqueous or mixed aqueous organic or organic solution). The deposited coating may form a thin layer on the surface of the agricultural product that may protect the agricultural product from biotic stress sources, water loss, and/or oxidation. In some embodiments, the deposited coating may have a thickness of less than 10 microns, less than 9 microns, less than 8 microns, less than 7 microns, less than 6 microns, less than 5 microns, less than 4 microns, less than 3 microns, less than 2 microns, or less than about 1500nm, and/or the coating may be transparent to the naked eye. For example, the deposited coating may have a thickness of about 10nm, about 20nm, about 30nm, about 40nm, about 50nm, about 100nm, about 150nm, about 200nm, about 250nm, about 300nm, about 350nm, about 400nm, about 450nm, about 500nm, about 550nm, about 600nm, about 650nm, about 700nm, about 750nm, about 800nm, about 850nm, about 900nm, about 950nm, 1,000nm, about 1,100nm, about 1,200nm, about 1,300nm, about 1,400nm, about 1,500nm, about 1,600nm, about 1,700nm, about 1,800nm, about 1,900nm, about 2,000nm, about 2,100nm, about 2,200nm, about 2,300nm, about 2,400nm, about 2,500nm, about 2,600nm, about 2,700nm, about 2,800nm, about 2,900nm, about 2,000nm, or about 3,000nm (including all ranges therebetween).
In some embodiments, the deposited coating may be substantially uniformly deposited on the substrate and may be free of defects and/or pinholes. In some embodiments, the dip coating process may include successive applications of the agricultural product in a bath of coating precursors that can self-assemble or covalently bond on the agricultural product to form the coating. In some embodiments, the coating may be deposited on the agricultural product by passing the agricultural product under a coating solution/suspension/colloid flow (e.g., a coating solution/suspension/colloid waterfall). For example, the agricultural product may be placed on a conveyor that passes through the flow of coating solution/suspension/colloid. In some embodiments, the coating may be atomized, vapor deposited, or dry vapor deposited on the surface of the agricultural product. In some embodiments, the coating solution/suspension/colloid may be mechanically applied to the surface of the product to be coated, for example, by brushing it onto the surface. In some embodiments, the coating may be configured to be immobilized on the surface of the agricultural product by UV crosslinking or by exposure to a reactive gas (e.g., oxygen).
In some embodiments, the coating solution/suspension/colloid may be sprayed onto the agricultural product. The coating solution/suspension/colloid can be sprayed onto the agricultural product using a commercially available sprayer. In some embodiments, the coating formulation may be charged in a sprayer prior to spraying it onto the agricultural product, such that the deposited coating is electrostatically and/or covalently bonded to the outer surface of the agricultural product.
As previously described, the coating formed by the coating agents described herein may be configured to prevent moisture loss or other moisture loss from the coated portion of the plant, delay ripening, and/or prevent oxygen from diffusing into the coated portion of the plant to reduce oxidation of the coated portion of the plant. The coating may also act as a barrier to the diffusion of carbon dioxide and/or ethylene into or out of the plant or agricultural product. The coating may also protect the coated portion of the plant from biotic stressors such as bacteria, fungi, viruses, and/or pests that may infect and degrade the coated portion of the plant. Since bacteria, fungi and pests all determine the source of food by identifying specific molecules on the surface of the agricultural product, coating the agricultural product with the coating agent can deposit molecularly opposite molecules on the surface of the portion of the plant, thereby making the agricultural product unrecognizable. In addition, the coating may also alter the physical and/or chemical environment of the surface of the agricultural product, thereby rendering the surface less conducive to bacterial, fungal, or pest growth. The coating may also be formulated to protect the surface of the portion of the plant from abrasion, bruising, or other mechanical damage, and/or to protect the portion of the plant from photo-degradation. The part of the plant may include, for example, leaves, stems, buds, flowers, fruits, roots, and the like.
Any of the coatings described herein can be used to reduce the moisture generated by the agricultural product (e.g., fresh produce) through mass loss (e.g., moisture loss) during transport and storage by reducing the rate of mass loss of the agricultural product (e.g., fresh produce). For example, as shown in example 16, a group of lemons coated with a 94:6 mixture of 50G/L of a compound of formula I (SA-1G and PA-1G) and a compound of formula II or III (SA-Na) in water had a mass loss rate of 0.37% per day, while the untreated control group was 1.61% per day. This corresponds to a lower humidity (i.e. 61% humidity) for the coated group after 48 hours of refrigeration, while the humidity for the untreated group was 72%.
In some embodiments, the agricultural product is coated with a composition that reduces the rate of mass loss by at least 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75%, 80%, 85%, 90% or more compared to the untreated product as measured. In some embodiments, treating an agricultural product with any of the coatings described herein can result in a quality loss factor of at least 1.1, at least 1.2, at least 1.3, at least 1.4, at least 1.5, at least 1.6, at least 1.7, at least 1.8, at least 1.9, at least 2.0, at least 2.2, at least 2.4, at least 2.6, at least 2.8, at least 3.0. In some embodiments, treating an agricultural product with any of the coatings described herein can reduce the humidity generated during storage by at least 1%, 2%, 3%, 4%, 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75%, 80%, 85%, 90% or more compared to an untreated product. In some embodiments, reducing the rate of mass loss of the agricultural product can reduce the energy required to maintain the relative humidity at a predetermined level (e.g., 90% relative humidity or less, 85% relative humidity or less, 80% relative humidity or less, 75% relative humidity or less, 70% relative humidity or less, 65% relative humidity or less, 60% relative humidity or less, 55% relative humidity or less, 50% relative humidity or less, or 45% relative humidity or less). In some embodiments, the energy required to maintain the relative humidity at a predetermined level (e.g., any of the predetermined levels listed above) during storage or transport can be reduced by at least 1%, 2%, 3%, 4%, 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75%, 80%, 85%, 90% or more as compared to the untreated product.
Any of the coatings described herein can be used to reduce the heat generated by respiration of agricultural products (e.g., fresh produce) during transportation and storage by reducing the respiration rate of the agricultural products (e.g., fresh produce). As shown in example 17, the energy for maintaining the temperature (16 ℃) of a group of avocados coated with a 94:6 mixture of compounds of formula I (SA-1G and PA-1G) and compounds of formula II or III (SA-Na) in water at 50G/L was 0.85kWh for 72 hours, while the untreated control group was 1.19 kWh. In some embodiments, the product is coated with a composition that reduces the respiration rate by at least 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75%, 80%, 85%, 90% or more as compared to an untreated product (measured as described above). In some embodiments, reducing the heat generated by the agricultural product can reduce the energy required to maintain the temperature (e.g., a predetermined temperature) during storage or transportation. In some embodiments, the heat generated by the coated product can be reduced by at least 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75%, 80%, 85%, 90% or more as compared to an untreated product. In some embodiments, the energy required to maintain the coated product at a predetermined temperature (e.g., 25 ℃ or less, 23 ℃ or less, 20 ℃ or less, 18 ℃ or less, 15 ℃ or less, 13 ℃ or less, 10 ℃ or less, 8 ℃ or less, 5 ℃ or less, or 3 ℃ or less) can be reduced by at least 1%, 2%, 3%, 4%, 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75%, 80%, 85%, 90% or more compared to the untreated product.
The respiration rate approximation for various types of agricultural products (e.g., fresh produce) is as follows:
type of agricultural product Respiration Rate (ml CO) at 20 deg.C2/kg hour)
Apple (Malus pumila) 10-30
Apricot 15-25
Asparagus officinalis 138-250
Avocado 40-150
Banana 20-70
Broccoli (Broccoli) 140-160
Hami melon 23-33
Cherry 22-28
Corn (corn) 268-311
Cucumber (Cucumis sativus) 7-24
Fig fruit 20-30
Grape 12-15
Grapefruit 7-12
White melon 20-27
Kiwi fruit 15-20
Lemon 10-14
Sour orange 6-10
Citrus fruit 10-15
Mango (mango) 35-80
Orange 11-17
Pawpaw 15-35 (at 15 deg.C)
Peach shape 32-55
Pear (pear) 15-35
Pea (Pisum sativum L.) 123-180
Pineapple 15-20
Strawberry 50-100
Tomato 12-22
Watermelon 17-25
In some embodiments, the methods and compositions described herein are used to treat agricultural products (e.g., fresh agricultural produce) stored and/or transported in a refrigerated container or "fridge" 2400, as schematically illustrated in fig. 24. As shown in fig. 24, the heat generated by the produce respiration is the source of the total heat within the refrigerated container. In some embodiments, the methods and compositions described herein can reduce the respiration rate of a treated agricultural product (e.g., fresh produce) in order to reduce the heat generated as a result of the respiration of the agricultural product (e.g., fresh produce) in a refrigerated container or "cooler. In some embodiments, the methods and compositions described herein can reduce the rate of quality loss of treated agricultural products (e.g., fresh produce) in order to reduce the humidity generated as a result of the quality loss (e.g., moisture loss) of agricultural products (e.g., fresh produce) in a refrigerated container or "freezer.
The methods and compositions described herein can also be used to minimize or reduce temperature or humidity gradients that result from the concentration of agricultural products (e.g., fresh produce) in stacks or pallets to prevent uneven ripening. The treated agricultural products (e.g., fresh produce) can be stacked vertically during storage, or can be stacked in an alternative manner (e.g., laterally stacked) to increase circulation around the agricultural products (e.g., fresh produce). In the agricultural product supply chain, agricultural product boxes may be reoriented from a vertical stack (which may be preferred during transport) to a lateral stack (which is used during storage) to increase air circulation and prevent uneven ripening. As shown in FIG. 25 and example 18, coating an agricultural product with a 94:6 mixture of compounds of formula I (PA-1G and SA-1G) and compounds of formula II or III (SA-Na) reduced the rate of temperature rise in the avocado box stack after removal from the 10 ℃ storage. As shown in fig. 25, the rate of temperature rise of the treated produce after removal from the 10 ℃ freezer slowed down within the first three days after removal. Untreated vertically stacked and laterally stacked agricultural produce generates more heat under ambient storage conditions within the first three days than treated vertically stacked agricultural produce, with untreated vertically stacked agricultural produce generating the most heat. Therefore, the temperature gradient across the pallet should also be reduced to achieve more uniform and predictable ripening. In some embodiments, coating agricultural products with a coating composition that reduces the heat generated within a stack of agricultural products (e.g., heat generated by respiration) can reduce labor requirements throughout the agricultural product supply chain by minimizing the need to reorient the stack from a vertical stack to an alternate stack (e.g., a lateral stack).
In some embodiments, treating the agricultural product with a coating that reduces the rate of temperature increase in the stack (e.g., after removal from a refrigerator) can reduce the rate of temperature increase in the stack by at least 0.5 ℃ per day, at least 1.0 ℃ per day, at least 1.5 ℃ per day, at least 2.0 ℃ per day, at least 2.5 ℃ per day, at least 3.0 ℃ per day, at least 3.5 ℃ per day, at least 4.0 ℃ per day, at least 4.5 ℃ per day, or at least 5 ℃ per day, as compared to an untreated stack. In some embodiments, treating the agricultural product with the respiration rate-reducing coating can reduce the equilibrium temperature difference between the atmosphere and the average temperature of the stack by at least 0.5 ℃, at least 1.0 ℃, at least 1.5 ℃, at least 2.0 ℃, at least 2.5 ℃, at least 3.0 ℃, at least 3.5 ℃, at least 4.0 ℃, at least 4.5 ℃ or at least 5 ℃.
Any of the coatings described herein can be used to protect any agricultural product. In some embodiments, the coating may be applied to edible agricultural products, such as fruits, vegetables, edible seeds and nuts, herbs, spices, agricultural products, meats, eggs, dairy products, seafood, grains, or any other consumable. In such embodiments, the coating may include components that are non-toxic and safe for human and/or animal consumption. For example, the coating may include the following components: the Food and Drug Administration (FDA) approved direct or indirect food additives, FDA approved food contact substances, components that meet FDA regulatory requirements for use as food additives or food contact substances, and/or components that are FDA recognized as safe (GRAS) materials. Examples of such materials can be found in FDA Federal regulations Collection 21 at "http:// www.accessdata.fda.gov/scripts/cdrh/cfdocs/cfcf/cfrseearch.cfm" (the entire contents of which are hereby incorporated by reference). In some embodiments, the components of the coating may comprise a dietary supplement or a component of a dietary supplement. The components of the coating may also include FDA approved food additives or color additives. In some embodiments, the coating may include components of natural origin, as described herein. In some embodiments, the coating may be odorless or have a high flavor threshold of less than 500ppm, odorless or have a high odor threshold and/or substantially transparent. In some embodiments, the coating may be configured to be rinsed off of the edible agricultural product, for example, with water.
In some embodiments, the coatings described herein may be formed on non-edible agricultural products. Such non-edible agricultural products may include, for example, non-edible flowers, seeds, buds, stems, leaves, whole plants, and the like. In such embodiments, the coating may comprise a non-toxic component, but the threshold level of non-toxicity may be higher than the threshold level specified for edible products. In such embodiments, the coating may comprise an FDA-approved food contact substance, an FDA-approved food additive, or an FDA-approved pharmaceutical ingredient, such as any of those included in the FDA's approved drug database, which may be found in "http:// www.accessdata.fda.gov/scripts/cder/drug ftda/index. In some embodiments, the coating may comprise materials that meet FDA requirements for use in a drug or are listed in FDA national drug discovery code catalog "http:// www.accessdata.fda.gov/scripts/cder/ndc/default.cfm" (the entire contents of which are hereby incorporated herein by reference). In some embodiments, the material may comprise inactive pharmaceutical ingredients of approved pharmaceutical products listed in the FDA database "http:// www.accessdata.fda.gov/scripts/cder/ndc/default. cfm" (the entire contents of which are hereby incorporated herein by reference).
Embodiments of the coatings described herein have several advantages, including, for example: (1) the coating can protect the agricultural product from biotic stressors (i.e., bacteria, viruses, fungi, or pests); (2) the coating can prevent evaporation of water and/or diffusion of oxygen, carbon dioxide and/or ethylene; (3) the coating can help extend the shelf life of agricultural products (e.g., post-harvest produce) without refrigeration; (4) the coating can introduce mechanical stability to the surface of the agricultural product, thereby eliminating the need for expensive packaging of the scratch type designed to prevent accelerated spoilage; (5) the use of agricultural waste to obtain coatings can help eliminate the breeding environment for bacteria, fungi and pests; (6) the coating can be used to protect plants in place of pesticides, thereby minimizing the harmful effects of pesticides on human health and the environment; (7) the coating may be of natural origin and is therefore safe for human consumption. Because in some cases, the components of the coatings described herein are available from agricultural waste, such coatings can be made at relatively low cost. Thus, the coating may be particularly suitable for small-scale farmers, for example, by reducing the cost required to protect crops from pesticides and reducing post-harvest losses of agricultural products due to decomposition of biological and/or environmental stressors.
Due to market segments, the preparation/formation of coating agents or coating solutions/suspensions/colloids and the formation of coatings on substrates from coating solutions/suspensions/colloids are often performed by different parties or entities. For example, a manufacturer (i.e., a first party) of a composition (such as a coating agent described herein) can form the composition by one or more of the methods described herein. The resulting composition may then be sold or otherwise provided by the manufacturer to a second party, such as a farmer, shipper, distributor or retailer of agricultural products, and the second party may apply the composition to one or more agricultural products to form a protective coating on the products. Alternatively, the manufacturer may sell or otherwise provide the resulting composition to an intermediate party, such as a wholesaler, and the composition is then sold or otherwise provided by the intermediate party to a second party, such as a farmer, shipper, distributor or retailer of agricultural products, and the second party may apply the composition to one or more agricultural products to form a protective coating on the products.
In some cases involving multiple parties, the first party may optionally provide instructions or advice (written or oral) regarding the composition (i.e., coating agent), indicating one or more of: (i) the composition is intended to be applied to a product for the purpose of coating or protecting the product, extending the life of the product, reducing spoilage of the product, or altering or improving the aesthetic appearance of the product; (ii) conditions and/or methods suitable for applying the composition to the surface of the product; and/or (iii) potential benefits that may result from applying the composition to a product (e.g., increased shelf life, reduced rate of quality loss, reduced rate of mold and/or spoilage, etc.). Although instructions or suggestions may be provided by the first party directly with the plant extract composition (e.g., on the package of the composition being sold or distributed), the instructions or suggestions may alternatively be provided separately, e.g., on a website owned or controlled by the first party, or in advertising or marketing material provided by or on behalf of the first party.
In view of the foregoing, it is recognized that in some instances, one party (i.e., a first party) making a composition (i.e., a coating agent) or a coating solution/suspension/colloid according to one or more methods described herein may not form a coating directly on a product from the composition, but may direct (e.g., may indicate or require) a second party to form a coating on a product from the composition. That is, even if the first party does not coat the product by the methods and compositions described herein, the first party may still have the coating agent or solution applied to the product by providing instructions or suggestions as described above to form a protective coating on the product. Thus, as used herein, the act of applying a coating agent or solution/suspension/colloid to a product (e.g., a plant or agricultural product) also includes directing or instructing another party to apply the coating agent or solution to the product such that the coating agent or solution is applied to the product.
Examples
The following examples describe the effect of various coating agents and solutions/suspensions/colloids on various substrates, and the characterization of some of the various coating agents and solutions/suspensions/colloids. These examples are for illustrative purposes only and are not intended to limit the scope of the present disclosure. In each of the following examples, all reagents and solvents were purchased and used without further purification unless otherwise indicated.
Example 1: effect of coating formed from Long-chain fatty acid ester on quality loss Rate of finger orange
FIG. 1 is a graph showing the average daily mass loss rate of finger oranges coated with various mixtures of PA-2G and PA-1G measured over several days. Each bar in the graph represents the average daily mass loss rate for a group of 24 finger oranges. The finger corresponding to bar 102 was untreated. The fingers corresponding to bar 104 were coated with a substantially pure coating agent of PA-1G. The finger orange corresponding to bar 106 was coated with a coating agent of about 75% PA-1G and 25% PA-2G by mass. The finger orange corresponding to bar 108 was coated with a coating agent of about 50% PA-1G and 50% PA-2G by mass. The finger orange corresponding to the bar 110 was coated with a coating agent of about 25% PA-1G and 75% PA-2G by mass. The fingers corresponding to bar 112 were coated with a substantially pure coating agent of PA-2G. The coating agents were each dissolved in ethanol at a concentration of 10mg/mL to form a solution, and then the solution was applied onto the surface of the corresponding finger orange to form a coating layer.
To form the coating, the orange was placed in a bag and the solution containing the composition was poured into the bag. The bag was then sealed and gently shaken until the entire surface of each finger orange was wet. The finger oranges were then removed from the bag and allowed to dry on a drying rack. During drying and throughout the test, it will be referred to that the oranges are maintained at ambient room conditions of a temperature of about 23 ℃ to 27 ℃ and a humidity of about 40% to 55%.
As shown in fig. 1, untreated finger oranges (102) exhibited a mean mass loss rate of 5.3% per day. The mass loss rates of orange coated with the substantially pure PA-1G formulation (104) and the substantially pure PA-2G formulation (112) showed average daily mass loss rates of 4.3% and 3.7%, respectively. The orange group corresponding to bar 106 (75: 25 mass ratio of PA-1G to PA-2G) and bar 108 (50: 50 mass ratio of PA-1G to PA-2G) each exhibited an average daily mass loss rate of 3.4%. The finger oranges corresponding to bar 110 (25: 75 mass ratio of PA-1G to PA-2G) showed an average daily mass loss of 2.5%.
Example 2: effect of coatings formed from Long-chain fatty acids and/or esters thereof on the loss of Mass Rate of avocados
Nine solutions using combinations of long chain fatty acid esters were prepared to examine the effect of various coating agent compositions on the rate of mass loss of avocados treated with solutions consisting of a coating agent dissolved in a solvent to form a coating on the avocados. Each solution consisted of the following coating agents dissolved in ethanol at a concentration of 5 mg/mL.
The first solution comprised MA-1G and PA-2G combined in a molar ratio of 1: 3. The second solution contained MA-1G and PA-2G combined in a molar ratio of 1: 1. The third solution contained MA-1G and PA-2G combined in a molar ratio of 3: 1. The fourth solution contained PA-1G and PA-2G combined in a molar ratio of 3: 1. The fifth solution contained PA-1G and PA-2G combined in a molar ratio of 1: 1. The sixth solution contained PA-1G and PA-2G combined in a molar ratio of 1: 3. The seventh solution comprised SA-1G and PA-2G combined in a molar ratio of 1: 3. The eighth solution contained SA-1G and PA-2G combined in a molar ratio of 1: 1. The ninth solution contained SA-1G and PA-2G combined in a molar ratio of 3: 1.
Avocados were harvested simultaneously in nine groups of 30 avocados each, each group being identical in quality (i.e., the average size and quality of the avocados across all groups being approximately the same). To form the coating, the avocados were immersed in one of the solutions, and 30 avocados per group were treated with the same solution. The avocados are then placed on a drying rack and allowed to dry at ambient room conditions of a temperature of about 23 ℃ to 27 ℃ and a relative humidity of about 40% to 55%. The avocados were maintained under the same conditions of temperature and humidity throughout the test.
Fig. 2 is a graph showing the mass loss factor of avocados coated with the various solutions described above. Bars 202, 204, and 206 correspond to MA-1G and PA-2G (first solution, second solution, and third solution), respectively, combined in a molar ratio of about 1:3, 1:1, and 3: 1. Bars 212, 214, and 216 correspond to PA-1G and PA-2G (fourth solution, fifth solution, and sixth solution), respectively, combined at about 1:3, 1:1, and 3:1 molar ratios. Bars 222, 224, and 226 correspond to SA-1G and PA-2G (seventh solution, eighth solution, and ninth solution), respectively, combined at about 1:3, 1:1, and 3:1 molar ratios.
As shown in fig. 2, the treatment is performed in the first solution (202) so that the mass loss factor is 1.48, the treatment is performed in the second solution (204) so that the mass loss factor is 1.42, the treatment is performed in the third solution (206) so that the mass loss factor is 1.35, the treatment is performed in the fourth solution (212) so that the mass loss factor is 1.53, the treatment is performed in the fifth solution (214) so that the mass loss factor is 1.45, the treatment is performed in the sixth solution (216) so that the mass loss factor is 1.58, the treatment is performed in the seventh solution (222) so that the mass loss factor is 1.54, the treatment is performed in the eighth solution (224) so that the mass loss factor is 1.47, and the treatment is performed in the ninth solution (226) so that the mass loss factor is 1.52.
Fig. 3 is a graph showing the mass loss factors for avocados each coated with a mixture comprising a long chain fatty acid ester and a long chain fatty acid. All mixtures were mixtures with a molar ratio of compound fatty acid ester to fatty acid of 1: 1. The bars 301-303 correspond to coating agents consisting of MA-1G and MA (301), MA-1G and PA (302), and MA-1G and SA (303). The bars 311 & 313 correspond to the coating agents consisting of PA-1G & MA (311), PA-1G & PA (312), and PA-1G & SA (313). The bars 321-323 correspond to coating agents consisting of SA-1G and MA (321), SA-1G and PA (322), and SA-1G and SA (323). Each bar in the figure represents a group of 30 avocados. All coatings were formed by: avocados are immersed in a solution containing the relevant mixture dissolved in ethanol at a concentration of 5mg/mL, placed on a drying rack, and allowed to dry under ambient room conditions of a temperature of about 23 ℃ to 27 ℃ and a humidity of about 40% to 55%. The avocados were maintained under the same conditions of temperature and humidity throughout the test.
As shown, the mass loss factor tends to increase with increasing carbon chain length of the fatty acid ester. For example, all mixtures with esters having carbon chain lengths greater than 13 result in mass loss factors greater than 1.2, all mixtures with esters having carbon chain lengths greater than 15 result in mass loss factors greater than 1.35, and all mixtures with esters having carbon chain lengths greater than 17 result in mass loss factors greater than 1.6.
Fig. 4 is a graph showing the mass loss factor for avocados each coated with a coating agent comprising two different long chain fatty acid ester compounds mixed in a 1:1 molar ratio. Bar 402 corresponds to a mixture of SA-1G and PA-1G, bar 404 corresponds to a mixture of SA-1G and MA-1G, and bar 406 corresponds to a mixture of PA-1G and MA-1G. Each bar in the figure represents a group of 30 avocados. All coatings were formed by: the avocados were immersed in a solution consisting of the relevant mixture dissolved in ethanol at a concentration of 5mg/mL, placed on a drying rack, and allowed to dry under ambient room conditions of a temperature of about 23 ℃ to 27 ℃ and a humidity of about 40% to 55%. The avocados were maintained under the same conditions of temperature and humidity throughout the test. As shown, the PA-1G/MA-1G mixture (406) results in a mass loss factor of 1.47, the SA-1G/PA-1G mixture (402) results in a mass loss factor of 1.54, and the SA-1G/MA-1G mixture (1604) results in a mass loss factor of 1.60.
Example 3: effect of coating agent concentration on quality loss Rate of coated blueberry
Two solutions were prepared by dissolving a coating agent formed from PA-2G and PA-1G mixed in a mass ratio of 75:25 in substantially pure ethanol. For the first solution, the coating agent was dissolved in ethanol at a concentration of 10mg/mL, and for the second solution, the coating agent was dissolved in ethanol at a concentration of 20 mg/mL.
The blueberries were harvested simultaneously in three groups of 60 blueberries each, each group being identical in quality (i.e. the average size and quality of the blueberries of all groups was approximately the same). The first group was an untreated control of blueberries, the second group was treated with 10mg/mL solution, and the third group was treated with 20mg/mL solution.
To process the blueberries, each blueberry was picked up with a set of tweezers, dipped into the solution separately for approximately 1 second, and then placed on a drying rack and allowed to dry. The blueberries were maintained at ambient room conditions of 23-27 ℃ and 40-55% humidity during drying and throughout the test. Mass loss was measured by carefully weighing the blueberries daily, with the reported mass loss percentage being equal to the ratio of mass loss to initial mass.
FIG. 6 shows a graph of the percent mass loss of untreated (control) blueberries (602), blueberries treated with a first solution of 10mg/mL (604), and blueberries treated with a second solution of 20mg/mL (606) over a 5 day period. As shown, the percentage mass loss after 5 days for untreated blueberries was 19.2%, while the percentage mass loss after 5 days for blueberries treated with 10mg/mL solution was 15% and the percentage mass loss after 5 days for blueberries treated with 20mg/mL solution was 10%.
Example 4: effect of coatings formed from esters and salts of Long-chain fatty acids on the Mass loss Rate of lemon
Fig. 7 is a graph showing the mass loss factors of lemons each coated with a coating agent including SA-1G and SA-Na mixed at a 4:1 mass ratio. Bar 702 corresponds to untreated lemons (control), bar 704 to lemons treated with a suspension consisting of a coating agent suspended in water at a concentration of 10mg/mL, bar 706 to lemons treated with a suspension consisting of a coating agent suspended in water at a concentration of 20mg/mL, bar 708 to lemons treated with a suspension consisting of a coating agent suspended in water at a concentration of 30mg/mL, bar 710 to lemons treated with a suspension consisting of a coating agent suspended in water at a concentration of 40mg/mL, and bar 712 to lemons treated with a suspension consisting of a coating agent suspended in water at a concentration of 50 mg/mL.
Each bar in the figure represents a group of 90 lemons. All coatings were formed by: lemons are immersed in their associated suspension, placed on a drying rack, and allowed to dry under ambient room conditions at a temperature of about 23-27 ℃ and a humidity of about 40% -55%. The lemons were kept under the same temperature and humidity conditions throughout the test. As shown in FIG. 7, the mass loss factor for lemon (704) treated with 10mg/mL solution was 1.83, the mass loss factor for lemon (706) treated with 20mg/mL solution was 1.75, the mass loss factor for lemon (708) treated with 30mg/mL solution was 1.90, the mass loss factor for lemon (710) treated with 40mg/mL solution was 1.78, and the mass loss factor for lemon (712) treated with 50mg/mL solution was 1.83.
Example 5: of the rate of mass loss of lemon by a coating formed from esters/salts of long chain fatty acids and esters of medium chain esters Influence of
Fig. 8 is a graph showing the mass loss factor of lemons treated with various coating agents suspended in water. Bar 802 corresponds to untreated lemons. Bar 804 corresponds to the coating agent formed by SA-1G and MA-Na mixed in a mass ratio of 95:5 and added to water at a concentration of 10 mg/mL. Bar 806 corresponds to the coating agent formed by SA-1G and MA-Na mixed in a mass ratio of 95:5 and added to water at a concentration of 30 mg/mL. Bar 808 corresponds to a coating formed from 10mg/mL SA-1G and MA-Na (mixed at a mass ratio of 95: 5) and 5mg/mL UA-1G suspended in water. Bar 810 corresponds to a coating formed from 30mg/mL SA-1G and MA-Na (mixed in a mass ratio of 95: 5) and 5mg/mL UA-1G suspended in water.
Each bar in the figure represents a group of 60 lemons. All coatings were formed by: lemons are immersed in their associated solutions, placed on drying racks, and allowed to dry under ambient room conditions at a temperature of about 23-27 ℃ and a humidity of about 40% -55%. The lemons were kept under the same temperature and humidity conditions throughout the test. As shown in fig. 8, the quality loss factor for the lemons corresponding to bar 804 is 1.50, the quality loss factor for the lemons corresponding to bar 806 is 1.68, the quality loss factor for the lemons corresponding to bar 808 is 1.87, and the quality loss factor for the lemons corresponding to bar 810 is 2.59.
Example 6: contact angle of solvent and mixture on lemon surface
Fig. 10 shows a graph of contact angles of various solvents or mixtures on an unsalexed lemon surface. The contact angle was determined by: a drop containing 5 microliters of solvent/mixture was placed on the lemon surface and the contact angle was determined by digital image analysis. Each bar in the graph represents the measurement of 15-20 drops. For bar 1002, the solvent was pure water (control sample). For bar 1004, the mixture includes SA-1G and MA-Na combined in a 95:5 mass ratio and dispersed in water at a concentration of 30 mg/mL. The mixture corresponding to bars 1006, 1008, 1010, 1012, 1014, and 1016 is the same as the mixture of bar 1004, but also includes a low concentration of CA-1G. Bar 1006 includes 0.1mg/mL CA-1G, bar 1008 includes 0.5mg/mL CA-1G, bar 1010 includes 1mg/mL CA-1G, bar 1012 includes 2mg/mL CA-1G, bar 1014 includes 4mg/mL CA-1G, and bar 1016 includes 6mg/mL CA-1G.
As shown in fig. 10, the droplets corresponding to the bars 1002 (pure water) exhibited an average contact angle of 88 ° on the lemons. The drop corresponding to bar 1004 (SA-1G/MA-Na in water) exhibited an average contact angle of 84 on the lemon. The drop corresponding to bar 1006 (with the addition of 0.1mg/mL CA-1G) exhibited an average contact angle of 70 on the lemon. The drop corresponding to bar 1008 (with 0.5mg/mL CA-1G added) exhibited an average contact angle of 68 on the lemon. The drop corresponding to bar 1010 (with 1mg/mL CA-1G added) exhibited an average contact angle of 65 on the lemon. The drop corresponding to bar 1012 (with 2mg/mL CA-1G added) exhibited an average contact angle on the lemon of 58 deg.. The drop corresponding to bar 1014 (with the addition of 4mg/mL CA-1G) exhibited an average contact angle of 56 on the lemon. The drop corresponding to bar 1016 (with the addition of 6mg/mL CA-1G) exhibited an average contact angle on the lemon of 47 deg..
Example 7: dependence of the carbon chain length of the surfactant on the contact angle of the mixture on the lemon surface
Fig. 11 shows a graph of the contact angle of various mixtures on an unsaled lemon surface. The contact angle was determined by: a drop containing 5 microliters of the mixture was placed on the lemon surface and the contact angle was determined by digital image analysis. Each bar in the graph represents the measurement of 15-20 drops. For bar 1102, the solvent was pure water (control sample). For bar 1104, the mixture included SA-1G and MA-Na combined in a 95:5 mass ratio and dispersed in water at a concentration of 30 mg/mL. The suspensions corresponding to bars 1106, 1108 and 1110 were the same as the suspension of bar 1104, but also included 4mg/mL of medium chain fatty acid ester. For bar 1106, the medium chain fatty acid ester is LA-1G (carbon chain length of 12), for bar 1108, the medium chain fatty acid ester is UA-1G (carbon chain length of 11), and for bar 1110, the medium chain fatty acid ester is CA-1G (carbon chain length of 10).
As shown in fig. 11, the droplets corresponding to bar 1102 (pure water) exhibited an average contact angle of 88 ° on the lemons. The drop corresponding to bar 1104 (SA-1G/MA-Na in water) exhibited an average contact angle of 84 on the lemon. The drop corresponding to bar 1106 (with 4mg/mL of LA-1G added) exhibited an average contact angle of 67 ° on the lemon. The drop corresponding to bar 1108 (with 4mg/mL of UA-1G added) exhibited an average contact angle of 56 ° on the lemon. The drop corresponding to bar 1110 (with 1mg/mL CA-1G added) exhibited an average contact angle of 50 on the lemon.
Example 8: solvents and mixtures on the surface of lemon, candelilla and carnauba waxesContact angle
FIG. 12 shows a graph of contact angles of various solvents and mixtures on the surface of unsaled lemon (1201-1203), candelilla wax (1211-1213) and carnauba wax (1221-1223). The contact angle was determined by: a drop containing 5 microliters of the solution was placed on the surface to be tested and the contact angle was determined by digital image analysis. Each bar in the graph represents the measurement of 15-20 drops. For bars 1201, 1211 and 1221, the solvent was pure water (control sample). The second set of bars (1202, 1212, and 1222) corresponded to 30mg/mL SA-1G and SA-Na combined at a mass ratio of 94:6, as well as 0.25mg/mL citric acid and 0.325mg/mL sodium bicarbonate dispersed in water. The third set of bars (1203, 1213 and 1223) corresponds to the same mixture as the second set of bars, but also includes 3mg/mL of CA-1G.
As shown in fig. 12, the drop corresponding to bar 1201 exhibited an average contact angle of 92 ° on the lemon. The droplets corresponding to the swath 1202 exhibited an average contact angle of 105 ° on the candelilla wax. The drop corresponding to bar 1203 showed an average contact angle of 96 ° on the carnauba wax. The droplets corresponding to bar 1211 exhibit an average contact angle on the lemon of 80 °. The drop corresponding to the strip 1212 exhibited an average contact angle of 87 ° on the candelilla wax. The droplets corresponding to bars 1213 exhibited an average contact angle of 88 ° on carnauba wax. The drop corresponding to bar 1221 exhibited an average contact angle of 44 on the lemon. The drop corresponding to bar 1222 exhibited an average contact angle of 31 ° on candelilla wax. The drop corresponding to bar 1223 exhibited an average contact angle of 32 ° on carnauba wax.
Example 9: adding medium-chain fatty acid esters to a coating mixture for forming a protective coating on avocados Influence of
FIG. 13 shows the mass loss factors for a group of avocados coated with coating agents comprising SA-1G and MA-Na mixed with various concentrations of CA-1G or LA-1G. Forming a coating by: each coating agent was added to water at the indicated concentration to form a mixture, the mixture was applied to the avocado surface, and the solvent was allowed to evaporate. Bar 1301 corresponds to untreated avocados (control). Bar 1302 corresponds to a coating agent comprising SA-1G and MA-Na combined in a mass ratio of 94:6 and added to water at a concentration of 30 mg/mL. For bars 1303 and 1313, the mixture was the same as that of bar 1302, except that 1mg/mL of CA-1G (bar 1303) or LA-1G (bar 1313) was also added. For bars 1304 and 1314, the mixture is the same as that of bar 1302, except that 2.5mg/mL of CA-1G (bar 1304) or LA-1G (bar 1314) is also added. For bars 1305 and 1315, the mixture was the same as that of bar 1302, except that 4mg/mL CA-1G (bar 1305) or LA-1G (bar 1315) was also added. Each bar in the figure represents a group of 30 avocados. All coatings were formed by: immersing the avocados in their associated mixture, placing the avocados on a drying rack, and drying the avocados under ambient room conditions of a temperature of about 23 ℃ to 27 ℃ and a humidity of about 40% to 55%. The avocados were maintained under the same conditions of temperature and humidity throughout the test.
As shown in fig. 13, the average mass loss factor for avocados corresponding to bar 1302 (without medium chain fatty acid esters) was 1.78. For the mixture containing a low concentration of CA-1G (bar 1303-. For mixtures containing low concentrations of LA-1G (bar 1313-1315), the average mass loss factor for coated avocados in bar 1313(LA-1G concentration of 1mg/mL) was 1.61, the average mass loss factor for coated avocados in bar 1314(LA-1G concentration of 2.5mg/mL) was 2.15, and the average mass loss factor for coated avocados in bar 1315(LA-1G concentration of 4mg/mL) was 2.15.
Example 10: effect of adding CA-1G to a coating mixture for forming a protective coating on cherries
FIG. 14 shows the mass loss factors for a group of cherries (Bing variety) coated with a coating agent comprising SA-1G and MA-Na mixed with various concentrations of CA-1G. Forming a coating by: each coating agent was dissolved in water at the specified concentration to form a solution, the solution was applied to the cherry surface, and the solvent was allowed to evaporate. Bar 1401 corresponds to untreated cherries (control). Bar 1402 corresponds to a coating agent comprising SA-1G and MA-Na combined in a mass ratio of 94:6 and suspended in water at a concentration of 40 mg/mL. For bar 1403, the suspension was the same as that of bar 1402, except that 0.5mg/mL CA-1G was also added. For bar 1404, the suspension was the same as that of bar 1402, except that 1mg/mL of CA-1G was also added. For bar 1405, the suspension was the same as that of bar 1402, except that 3mg/mL CA-1G was also added. Each bar in the figure represents a group of 90 cherries. All coatings were formed by: the cherries are immersed in their associated suspension, placed on a drying rack, and allowed to dry at ambient room conditions of a temperature of about 23 ℃ to 27 ℃ and a humidity of about 40% to 55%. The cherries were maintained under the same temperature and humidity conditions throughout the test.
As shown in fig. 14, the average mass loss factor for the cherries corresponding to bar 1402 (without medium chain fatty acid esters) was 1.60. For the suspension containing low concentrations of CA-1G (bar 1403-1405), the average mass loss factor for coated cherries of bar 1403(CA-1G concentration of 0.5mg/mL) was 1.75, the average mass loss factor for coated cherries of bar 1404(CA-1G concentration of 1mg/mL) was 1.96, and the average mass loss factor for coated cherries of bar 1405(CA-1G concentration of 3mg/mL) was 2.00.
Example 11: effect of adding UA-1G to a coating mixture for forming a protective coating on finger oranges
FIG. 15 shows the mass loss factors for orange group coated with coating agents comprising SA-1G and SA-Na mixed with various concentrations of UA-1G. Forming a coating by: each coating agent was added to water at the indicated concentration to form a suspension, the suspension was applied to the surface of the finger orange, and the solvent was allowed to evaporate. Bar 1501 corresponds to untreated finger oranges (control). Bar 1502 corresponds to a coating agent comprising SA-1G and SA-Na combined in a mass ratio of 94:6 and suspended in water at a concentration of 30 mg/mL. For bar 1503, the suspension was the same as that of bar 1502 except that 1mg/mL of UA-1G was also added. For bar 1504, the suspension was the same as that of bar 1502, except that 3mg/mL of UA-1G was also added. For strip 1505, the suspension was the same as for strip 1502, except that 5mg/mL of UA-1G was also added. Each bar in the figure represents a group of 48 finger oranges. All coatings were formed by: the finger oranges are immersed in their associated suspension, placed on a drying rack, and allowed to dry under ambient room conditions at a temperature of about 23 ℃ to 27 ℃ and a humidity of about 40% to 55%. Throughout the test, it will be referred to that the oranges are maintained under the same conditions of temperature and humidity.
As shown in fig. 15, the mean mass loss factor for the finger orange corresponding to bar 1502 (no medium chain fatty acid esters) is 1.61. For suspensions containing low concentrations of UA-1G (bar 1503 and 1505), coating of bar 1503(UA-1G concentration of 1mg/mL) indicated an orange average mass loss factor of 2.33, coating of bar 1504(UA-1G concentration of 3mg/mL) indicated an orange average mass loss factor of 2.06, and coating of bar 1505(UA-1G concentration of 5mg/mL) indicated an orange average mass loss factor of 1.93.
Example 12: effect of priming of Paraffin surface on contact Angle of solvent and mixture
Fig. 16 shows a graph of the contact angle of various solvents and mixtures on a paraffin surface. The contact angle was determined by: a drop containing 5 microliters of solvent/mixture was placed on the paraffin surface and the contact angle was determined by digital image analysis. Each bar in the graph represents the measurement of 15-20 drops. For bar 1601, the solvent was pure water. For bar 1602, the mixture includes SA-1G and SA-Na combined in a mass ratio of 95:5 and dispersed in water at a concentration of 45 mg/mL. The mixture corresponding to bar 1603 is the same as the mixture of bar 1602, but also includes 3mg/mL CA-1G. For strip 1604, a mixture of CA-1G in water at a concentration of 3mg/mL was first deposited on the surface of the paraffin and then allowed to dry to prime the surface. Thereafter, the contact angle of water on the primed surface is determined. For bar 1605, a mixture of CA-1G in water at a concentration of 3mg/mL is first deposited on the surface of the paraffin and then allowed to dry to prime the surface. Thereafter, the contact angle of the mixture of SA-1G and SA-Na dispersed in water at a concentration of 45mg/mL and a mass ratio of 95:5 on the primed surface was measured.
As shown in fig. 16, the droplet corresponding to the bar 1601 (pure water) exhibited an average contact angle of 74 ° on the paraffin. The droplet (mixture of SA-1G and SA-Na) corresponding to strip 1602 exhibited an average contact angle of 83 ° on paraffin. The droplet corresponding to bar 1603 (mixture of SA-1G, Sa-Na and CA-1G) exhibited an average contact angle on paraffin of 43 deg.. The droplet (pure water on the surface of the priming paraffin) corresponding to bar 1604 exhibited an average contact angle of 24 °. The droplets corresponding to bar 1605 (a mixture of SA-1G and SA-Na in water on the surface of the primed paraffin) exhibited an average contact angle of 30 °.
Example 13: effect of ester salt ratio in coating on avocado on Mass loss factor
FIG. 18 shows the mass loss factors for a group of avocados coated with coating agents comprising SA-Na or MA-Na combined in varying proportions with an approximately 50/50 mixture of SA-1G and PA-1G. Forming a coating by: each coating agent was added to water at a concentration of 30mg/mL to form a suspension, the suspension was applied to the avocado surface, and the solvent was allowed to evaporate. Bar 1801 corresponds to untreated avocados (control). The bar 1802 corresponds to a coating agent comprising a mixture of SA-1G/PA-1G and SA-Na combined in a mass ratio of 94: 6. The strip 1803 corresponds to a coating agent comprising a SA-1G/PA-1G mixture and SA-Na combined in a mass ratio of 70: 30. The strip 1804 corresponds to a coating agent comprising a SA-1G/PA-1G mixture and MA-Na combined in a mass ratio of 94: 6. The strip 1805 corresponds to a coating agent comprising a SA-1G/PA-1G mixture and MA-Na combined in a mass ratio of 70: 30. Each bar in the figure represents a group of 180 avocados. All coatings were formed by: the suspension is brushed onto the avocados, the avocados are placed on a drying rack, and the avocados are allowed to dry under ambient room conditions at a temperature of about 23 ℃ to 27 ℃ and a humidity of about 40% to 55%. The avocados were maintained under the same conditions of temperature and humidity throughout the test.
As shown in fig. 18, the average mass loss factor for the avocados corresponding to bar 1802 is 1.88, the average mass loss factor for the avocados corresponding to bar 1803 is 1.59, the average mass loss factor for the avocados corresponding to bar 1804 is 2.47, and the average mass loss factor for the avocados corresponding to bar 1805 is 1.91.
Example 14: effect of emulsifiers on the Mass loss Rate of avocados
FIG. 19 shows the mass loss rate of a group of avocados coated with a coating agent comprising a compound of formula II or III (SA-Na), a fatty alcohol derivative (sodium lauryl sulfate), or a phospholipid (lecithin) in combination with an approximately 50/50 mixture of SA-1G and PA-1G. All coatings were formed by: 28.2G/L of SA-1G and SA-Na (SA-1G/PA-1G mixture to SA-Na ratio 94:6), sodium lauryl sulfate (SA-1G/PA-1G mixture to SLS ratio 94:6) or lecithin (SA-1G/PA-1G mixture to lecithin ratio 70:30) were added to water to form a suspension, which was applied to the avocado surface and the solvent was allowed to evaporate. Bar 1901 corresponds to untreated avocados (control). Bar 1902 corresponds to a coating agent comprising a SA-1G/PA-1G mixture and SA-Na. Bar 1903 corresponds to a coating agent that includes the SA-1G/PA-1G mixture and SLS. Bar 1904 corresponds to a coating agent comprising the SA-1G/PA-1G mixture and soy lecithin. All coatings were formed by: the suspension is brushed onto the avocados, the avocados are placed on a drying rack, and the avocados are allowed to dry under ambient room conditions at a temperature of about 23 ℃ to 27 ℃ and a humidity of about 40% to 55%. The avocados were maintained under the same conditions of temperature and humidity throughout the test.
As shown in fig. 19, the loss rate of average volume of avocados corresponding to bar 1901 is 1.44% per day, the loss rate of average volume of avocados corresponding to bar 1902 is 0.88% per day, the loss rate of average volume of avocados corresponding to bar 1903 is 0.69% per day, and the loss rate of average volume of avocados corresponding to bar 1904 is 1.08% per day.
Example 15: effect of concentration and emulsifiers in the coating on avocado on respiration and Mass loss
FIG. 20 shows the mass loss factor for a group of avocados coated with a coating agent comprising SA-Na or Sodium Lauryl Sulfate (SLS) and an approximately 50/50 mixture of SA-1G and PA-1G. All coatings were formed using a SA-1G/PA-1G mixture with SA-Na or SLS in a ratio of 94: 6. Forming a coating by: each coating agent was added to water at a concentration of 20g/L, 30g/L, or 40g/L to form a suspension, the suspension was applied to the avocado surface, and the solvent was allowed to evaporate. Bar 2001 corresponds to a coating agent comprising a SA-1G/PA-1G mixture and 20G/L SA-Na. Bar 2002 corresponds to a coating agent that includes a SA-1G/PA-1G mixture and 20G/L SLS. Strip 2003 corresponds to a coating agent comprising a SA-1G/PA-1G mixture and 30G/L of SA-Na. Bar 2004 corresponds to a coating agent comprising a SA-1G/PA-1G mixture and 30G/L SLS. Bar 2005 corresponds to a coating agent comprising a SA-1G/PA-1G mixture and 40G/L SA-Na. Bar 2006 corresponds to a coating agent that includes a SA-1G/PA-1G mixture and 40G/L SLS. All coatings were formed by: the suspension is brushed onto the avocados, the avocados are placed on a drying rack, and the avocados are allowed to dry under ambient room conditions at a temperature of about 23 ℃ to 27 ℃ and a humidity of about 40% to 55%. The avocados were maintained under the same conditions of temperature and humidity throughout the test.
As shown in fig. 20, the mass loss factor of the avocado corresponding to bar 2001 is 1.57, the mass loss factor of the avocado corresponding to bar 2002 is 1.63, the mass loss factor of the avocado corresponding to bar 2003 is 1.64, the mass loss factor of the avocado corresponding to bar 2004 is 1.76, the mass loss factor of the avocado corresponding to bar 2005 is 1.81, and the mass loss factor of the avocado corresponding to bar 2006 is 1.88.
Figure 21 shows the same breathing factors for the avocado group as described above. Bar 2101 corresponds to a coating agent comprising a SA-1G/PA-1G mixture and 20G/L SA-Na. Bar 2102 corresponds to a coating agent that includes SA-1G/PA-1G mixture and SLS at 20G/L. Bar 2103 corresponds to a coating agent comprising a SA-1G/PA-1G mixture and 30G/L of SA-Na. Strip 2104 corresponds to a coating agent comprising a SA-1G/PA-1G mixture and 30G/L SLS. Bar 2105 corresponds to a coating agent comprising a SA-1G/PA-1G mixture and 40G/L SA-Na. Bar 2106 corresponds to a coating agent comprising SA-1G/PA-1G mixture and 40G/L SLS.
As shown in fig. 21, the respiration factor of the avocados corresponding to bar 2101 is 1.21, the respiration factor of the avocados corresponding to bar 2102 is 1.20, the respiration factor of the avocados corresponding to bar 2103 is 1.22, the respiration factor of the avocados corresponding to bar 2104 is 1.34, the respiration factor of the avocados corresponding to bar 2105 is 1.32, and the respiration factor of the avocados corresponding to bar 2102 is 1.41.
Fig. 22 and 23 show droplets of the coating mixture (i.e., coating agent in solvent) on the surface. The contact angle was determined by: a drop containing 5 microliters of the solution was placed on the surface to be tested and the contact angle was determined by digital image analysis. FIG. 22 corresponds to a representative image of a droplet comprising an 50/50 mixture of SA-1G and PA-1G and a coating mixture of SA-Na in a ratio of 94:6 in water at 45G/L. The contact angle observed from a coating mixture such as in fig. 22 was 95 ± 5 °. FIG. 23 corresponds to a representative image of a coating mixture of 50/50 mixture comprising SA-1G and PA-1G at a ratio of 94:6 in water and SLS at 45G/L. The contact angle observed from a coating mixture such as in fig. 23 is 84 ± 4 °.
Example 16: effect of coating on humidity during lemon refrigeration
Treatment group (lemon) Mass loss rate (% per day) Humidity (after 48 hours)
Untreated 1.61 72%
50g/L 0.37 61%
The table above shows a comparison between the mass loss rate and refrigeration humidity for untreated lemons and lemons treated with a 94:6 mixture of fatty acid ester (about 50/50 mixture of SA-1G and PA-1G) and fatty acid salt (SA-Na) in 50G/L water. Each treatment group comprised 7 bins of lemons, 60 lemons per bin. Each treatment group was placed in a box freezer equipped with a fan and a humidity sensor. As shown in the above table, the untreated group had a mass loss rate of 1.61% per day, while the lemons treated with the 50g/L mixture had a mass loss rate of 0.37% per day. The higher mass loss rate of the untreated group corresponds to a higher humidity in the box freezer, with 72% humidity in the freezer containing untreated lemons and 61% humidity in the freezer with lemons treated with 50g/L mix.
Example 17: effect of coating on energy usage during avocado refrigeration
Treatment group Energy usage after 72 hours (at 16 ℃ C.)
Untreated 1.19kWh
50g/L 0.85kWh
The table above shows a comparison between the energy usage of untreated avocados and avocados treated with a 94:6 mixture of fatty acid esters (an approximately 50/50 mixture of SA-1G and PA-1G) and fatty acid salts (SA-Na) in 50G/L water. Each treatment group included 7 cases of avocados, 60 avocados per case. Each treatment group was placed in a box freezer equipped with fans and energy usage. As shown in the table above, the freezer containing the untreated group consumed 1.19kWh of energy after 72 hours, while the freezer containing avocados treated with 50g/L of the mix consumed 0.85 kWh.
Example 18: temperature dependence of stack and coating
Fig. 25 is a graph showing the average temperature (deg.c) of three sample groups over about 5 days. Each sample set included 10 boxes of hasse avocados, 60 per box, stacked either vertically (i.e., 5 boxes high, 2 stacks wide, each box parallel to the underlying box stack) or laterally (i.e., 5 boxes high, 2 stacks wide, each box perpendicular to the underlying box stack). One of the vertical stacked groups (corresponding to 2502) was coated with a coating agent formed of SA-1G and SA-Na mixed at a mass ratio of 94:6 dispersed in water at a concentration of 30 mg/mL. The other groups were untreated avocados, stacked vertically (corresponding to 2501) or laterally (corresponding to 2503). In each group, the data represent the average temperature change over time for 4 temperature recorders distributed throughout the stack after removal from a 10 ℃ freezer.
As shown in fig. 25, the rate of temperature rise of the treated produce after removal from the 10 ℃ freezer was slowed compared to untreated produce over the first three days. Untreated vertically stacked and laterally stacked agricultural produce generates more heat under ambient storage conditions within the first three days than treated vertically stacked agricultural produce, with untreated vertically stacked agricultural produce generating the most heat. Therefore, the temperature gradient across the pallet should also be reduced to achieve more uniform and predictable ripening.
While various compositions and methods have been described above, it should be understood that they have been presented by way of example only, and not limitation. Where methods and steps described above indicate certain events occurring in a certain order, the order of the steps may be modified and such modifications are made in accordance with the variations of the present invention. Additionally, where possible, certain steps may be performed concurrently in a parallel process, as well as performed sequentially as described above. While various embodiments have been particularly shown and described, it will be understood that various changes in form and detail may be made. Accordingly, other implementations are within the scope of the following claims.

Claims (126)

1. A composition, comprising:
(i) from 50% to 99% by mass of a first group of compounds, wherein each compound of the first group is a compound of formula I; and
(ii) from 1% to 50% by mass of a second group of compounds, wherein each compound of the second group is a salt of formula II, wherein formulae I and II are:
Figure FDA0003045368930000011
wherein for each of the formulas:
R1、R2、R5、R6、R9、R10、R11、R12and R13Each occurrence of the formula is independently-H, - (C ═ O) R14、–(C=O)H、–(C=O)OH、–(C=O)OR14、–(C=O)-O-(C=O)R14、–O(C=O)R14、–OR14、–NR14R15、–SR14Halogen, -C1-C6Alkyl, -C2-C6Alkenyl, -C2-C6Alkynyl, -C3-C7Cycloalkyl, aryl OR heteroaryl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl OR heteroaryl is optionally substituted by one OR more-OR14、–NR14R15、–SR14Or halogen substitution;
R3、R4、R7and R8At each occurrence independently is-H, -OR14、–NR14R15、–SR14Halogen, -C1-C6Alkyl, -C2-C6Alkenyl, -C2-C6Alkynyl, -C3-C7A cycloalkyl group, an aryl group or a heteroaryl group,wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl OR heteroaryl is optionally substituted by-OR14、–NR14R15、–SR14Or halogen substitution; or
R3And R4May combine with the carbon atom to which they are attached to form C3-C6Cycloalkyl radical, C4-C6Cycloalkenyl or 3 to 6 membered ring heterocycle; and/or
R7And R8May combine with the carbon atom to which they are attached to form C3-C6Cycloalkyl radical, C4-C6Cycloalkenyl or 3 to 6 membered rings;
R14and R15Each occurrence independently is-H, aryl, heteroaryl, -C1-C6Alkyl, -C2-C6Alkenyl or-C2-C6An alkynyl group;
(symbol)
Figure FDA0003045368930000012
represents an optional single bond or a cis or trans double bond;
n is 0, 1,2, 3, 4, 5, 6, 7 or 8;
m is 0, 1,2 or 3;
q is 0, 1,2, 3, 4 or 5;
r is 0, 1,2, 3, 4, 5, 6, 7 or 8;
r is selected from-H, -glyceryl, -C1-C6Alkyl, -C2-C6Alkenyl, -C2-C6Alkynyl, -C3-C7Cycloalkyl, aryl or heteroaryl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl or heteroaryl is optionally substituted by one or more groups selected from halogen, hydroxy, nitro, -CN, -NH2、–SH、–SR15、–OR14、–NR14R15、–C1-C6Alkyl, -C2-C6Alkenyl or-C2-C6Radical substitution of alkynyl; and is
And X is a cationic part.
2. A composition, comprising:
(i) from 50% to 99% by mass of a first group of compounds, wherein each compound of the first group is a compound of formula I; and
(ii) 1 to 50% by mass of a second group of compounds, wherein each compound of the second group is a compound of formula III, wherein formula I and formula III are:
Figure FDA0003045368930000021
wherein for each of the formulas:
R1、R2、R5、R6、R9、R10、R11、R12and R13Each occurrence of the formula is independently-H, - (C ═ O) R14、–(C=O)H、–(C=O)OH、–(C=O)OR14、–(C=O)-O-(C=O)R14、–O(C=O)R14、–OR14、–NR14R15、–SR14Halogen, -C1-C6Alkyl, -C2-C6Alkenyl, -C2-C6Alkynyl, -C3-C7Cycloalkyl, aryl OR heteroaryl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl OR heteroaryl is optionally substituted by one OR more-OR14、–NR14R15、–SR14Or halogen substitution;
R3、R4、R7and R8At each occurrence independently is-H, -OR14、–NR14R15、–SR14Halogen, -C1-C6Alkyl, -C2-C6Alkenyl, -C2-C6Alkynyl, -C3-C7Cycloalkyl, aryl OR heteroaryl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl OR heteroaryl is optionally substituted with-OR14、–NR14R15、–SR14Or halogen substitution; or
R3And R4May combine with the carbon atom to which they are attached to form C3-C6Cycloalkyl radical, C4-C6Cycloalkenyl or 3 to 6 membered ring heterocycle; and/or
R7And R8May combine with the carbon atom to which they are attached to form C3-C6Cycloalkyl radical, C4-C6Cycloalkenyl or 3 to 6 membered rings;
R14and R15Each occurrence independently is-H, aryl, heteroaryl, -C1-C6Alkyl, -C2-C6Alkenyl or-C2-C6An alkynyl group;
(symbol)
Figure FDA0003045368930000031
represents an optional single bond or a cis or trans double bond;
n is 0, 1,2, 3, 4, 5, 6, 7 or 8;
m is 0, 1,2 or 3;
q is 0, 1,2, 3, 4 or 5;
r is 0, 1,2, 3, 4, 5, 6, 7 or 8;
r is selected from-H, -glyceryl, -C1-C6Alkyl, -C2-C6Alkenyl, -C2-C6Alkynyl, -C3-C7Cycloalkyl, aryl or heteroaryl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl or heteroaryl is optionally substituted by one or more groups selected from halogen, hydroxy, nitro, -CN, -NH2、–SH、–SR15、–OR14、–NR14R15、–C1-C6Alkyl, -C2-C6Alkenyl or-C2-C6Radical substitution of alkynyl; and is
Xp+Is a cationic counterion having a charge state p, and p is 1,2 or 3.
3. The composition of any one of claims 1-2, wherein each compound of the first set of compounds has a carbon chain length of at least 14.
4. The composition of claim 3, wherein each compound of the second group of compounds has a carbon chain length of at least 14.
5. The composition according to claim 4, wherein the composition comprises 70 to 99% by mass of the first group of compounds and 1 to 30% by mass of the second group of compounds.
6. The composition of any one of claims 1-2, wherein R is-glyceryl.
7. The composition of claim 6, wherein the second group of compounds comprises SA-Na, PA-Na, MA-Na, SA-K, PA-K, or MA-K.
8. The composition of any one of claims 1-2, wherein the mass ratio of the first group of compounds to the second group of compounds is in the range of 2 to 99.
9. The composition according to any one of claims 1-2, wherein the composition comprises less than 10% by mass of diglycerides.
10. The composition of any one of claims 1-2, wherein the composition comprises less than 10% by mass triglycerides.
11. The composition according to any one of claims 1-2, wherein the composition comprises less than 10% by mass of acetylated monoglycerides.
12. The composition of any one of claims 1-2, wherein the first set of compounds comprises one or more compounds selected from the group consisting of:
Figure FDA0003045368930000041
Figure FDA0003045368930000051
Figure FDA0003045368930000061
Figure FDA0003045368930000071
Figure FDA0003045368930000081
Figure FDA0003045368930000091
Figure FDA0003045368930000101
Figure FDA0003045368930000111
Figure FDA0003045368930000121
Figure FDA0003045368930000131
Figure FDA0003045368930000141
Figure FDA0003045368930000151
Figure FDA0003045368930000161
Figure FDA0003045368930000171
Figure FDA0003045368930000181
Figure FDA0003045368930000191
Figure FDA0003045368930000192
and
Figure FDA0003045368930000193
13. the composition of claim 2, wherein the second group of compounds comprises SA-Na, PA-Na, MA-Na, SA-K, PA-K or MA-K, (SA)2-Mg、(PA)2-Mg、(MA)2-Mg、(SA)2-Ca、(PA)2-Ca or (MA)2-Ca。
14. A mixture comprising a composition in a solvent, the composition comprising:
(i) from 50% to 99% by mass of a first group of compounds, wherein each compound of the first group is a compound of formula I;
(ii) from 1% to 50% by mass of a second group of compounds, wherein each compound of the second group is a salt of formula II, wherein formulae I and II are:
Figure FDA0003045368930000201
wherein for each of the formulas:
R1、R2、R5、R6、R9、R10、R11、R12and R13Each occurrence of the formula is independently-H, - (C ═ O) R14、–(C=O)H、–(C=O)OH、–(C=O)OR14、–(C=O)-O-(C=O)R14、–O(C=O)R14、–OR14、–NR14R15、–SR14Halogen, -C1-C6Alkyl, -C2-C6Alkenyl, -C2-C6Alkynyl, -C3-C7Cycloalkyl, aryl OR heteroaryl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl OR heteroaryl is optionally substituted by one OR more-OR14、–NR14R15、–SR14Or halogen substitution;
R3、R4、R7and R8At each occurrence independently is-H, -OR14、–NR14R15、–SR14Halogen, -C1-C6Alkyl, -C2-C6Alkenyl, -C2-C6Alkynyl, -C3-C7A cycloalkyl group, an aryl group or a heteroaryl group,wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl OR heteroaryl is optionally substituted by-OR14、–NR14R15、–SR14Or halogen substitution; or
R3And R4May combine with the carbon atom to which they are attached to form C3-C6Cycloalkyl radical, C4-C6Cycloalkenyl or 3 to 6 membered ring heterocycle; and/or
R7And R8May combine with the carbon atom to which they are attached to form C3-C6Cycloalkyl radical, C4-C6Cycloalkenyl or 3 to 6 membered rings;
R14and R15Each occurrence independently is-H, aryl, heteroaryl, -C1-C6Alkyl, -C2-C6Alkenyl or-C2-C6An alkynyl group;
(symbol)
Figure FDA0003045368930000202
represents an optional single bond or a cis or trans double bond;
n is 0, 1,2, 3, 4, 5, 6, 7 or 8;
m is 0, 1,2 or 3;
q is 0, 1,2, 3, 4 or 5;
r is 0, 1,2, 3, 4, 5, 6, 7 or 8;
r is selected from-H, -glyceryl, -C1-C6Alkyl, -C2-C6Alkenyl, -C2-C6Alkynyl, -C3-C7Cycloalkyl, aryl or heteroaryl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl or heteroaryl is optionally substituted by one or more groups selected from halogen, hydroxy, nitro, -CN, -NH2、–SH、–SR15、–OR14、–NR14R15、–C1-C6Alkyl, -C2-C6Alkenyl or-C2-C6Radical substitution of alkynyl; and is
And X is a cationic part.
15. A mixture comprising a composition in a solvent, the composition comprising:
(i) from 50% to 99% by mass of a first group of compounds, wherein each compound of the first group is a compound of formula I;
(ii) 1 to 50% by mass of a second group of compounds, wherein each compound of the second group is a compound of formula III, wherein formula I and formula III are:
Figure FDA0003045368930000211
wherein for each of the formulas:
R1、R2、R5、R6、R9、R10、R11、R12and R13Each occurrence of the formula is independently-H, - (C ═ O) R14、–(C=O)H、–(C=O)OH、–(C=O)OR14、–(C=O)-O-(C=O)R14、–O(C=O)R14、–OR14、–NR14R15、–SR14Halogen, -C1-C6Alkyl, -C2-C6Alkenyl, -C2-C6Alkynyl, -C3-C7Cycloalkyl, aryl OR heteroaryl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl OR heteroaryl is optionally substituted by one OR more-OR14、–NR14R15、–SR14Or halogen substitution;
R3、R4、R7and R8At each occurrence independently is-H, -OR14、–NR14R15、–SR14Halogen, -C1-C6Alkyl, -C2-C6Alkenyl, -C2-C6Alkynyl, -C3-C7Cycloalkyl, aryl or heteroaryl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl or heteroaryl isOptionally is-OR14、–NR14R15、–SR14Or halogen substitution; or
R3And R4May combine with the carbon atom to which they are attached to form C3-C6Cycloalkyl radical, C4-C6Cycloalkenyl or 3 to 6 membered ring heterocycle; and/or
R7And R8May combine with the carbon atom to which they are attached to form C3-C6Cycloalkyl radical, C4-C6Cycloalkenyl or 3 to 6 membered rings;
R14and R15Each occurrence independently is-H, aryl, heteroaryl, -C1-C6Alkyl, -C2-C6Alkenyl or-C2-C6An alkynyl group;
(symbol)
Figure FDA0003045368930000212
represents an optional single bond or a cis or trans double bond;
n is 0, 1,2, 3, 4, 5, 6, 7 or 8;
m is 0, 1,2 or 3;
q is 0, 1,2, 3, 4 or 5;
r is 0, 1,2, 3, 4, 5, 6, 7 or 8;
r is selected from-H, -glyceryl, -C1-C6Alkyl, -C2-C6Alkenyl, -C2-C6Alkynyl, -C3-C7Cycloalkyl, aryl or heteroaryl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl or heteroaryl is optionally substituted by one or more groups selected from halogen, hydroxy, nitro, -CN, -NH2、–SH、–SR15、–OR14、–NR14R15、–C1-C6Alkyl, -C2-C6Alkenyl or-C2-C6Radical substitution of alkynyl; and is
Xp+Is a cationic counterion having a charge state p, and p is 1,2 or 3.
16. The mixture of any one of claims 14-15, wherein the solvent is water.
17. The mixture of any one of claims 14-15, wherein the solvent is at least 50% water by volume.
18. The mixture of any one of claims 14-15, wherein the first set of compounds comprises one or more compounds selected from the group consisting of:
Figure FDA0003045368930000221
Figure FDA0003045368930000231
Figure FDA0003045368930000241
Figure FDA0003045368930000251
Figure FDA0003045368930000261
Figure FDA0003045368930000271
Figure FDA0003045368930000281
Figure FDA0003045368930000291
Figure FDA0003045368930000301
Figure FDA0003045368930000311
Figure FDA0003045368930000321
Figure FDA0003045368930000331
Figure FDA0003045368930000341
Figure FDA0003045368930000351
Figure FDA0003045368930000361
Figure FDA0003045368930000371
Figure FDA0003045368930000381
and
Figure FDA0003045368930000382
19. the mixture of any one of claims 14-15, wherein the second group of compounds comprises SA-Na, PA-Na, MA-Na, SA-K, PA-K, or MA-K.
20. The mixture of any one of claims 14-15, wherein the concentration of the composition in the mixture is in the range of 0.5 to 200 mg/mL.
21. A mixture according to any one of claims 14-15, wherein each compound of the first set of compounds has a carbon chain length of at least 14.
22. The mixture of claim 21, wherein each compound of the second set of compounds has a carbon chain length of at least 14.
23. The mixture according to claim 22, wherein the composition comprises 70 to 99% by mass of the first group of compounds and 1 to 30% by mass of the second group of compounds.
24. The mixture of any one of claims 14-15, wherein R is-glyceryl.
25. The mixture according to claim 15, wherein the second group of compounds comprises SA-Na, PA-Na, MA-Na, SA-K, PA-K, MA-K, (SA)2-Mg、(PA)2-Mg、(MA)2-Mg、(SA)2-Ca、(PA)2-Ca or (MA)2-Ca。
26. The mixture according to any one of claims 14-15, wherein the composition comprises less than 10% by mass of diglycerides.
27. The mixture of any one of claims 14-15, wherein the composition comprises less than 10% triglycerides by mass.
28. The mixture according to any one of claims 14-15, wherein the composition comprises less than 10% by mass of acetylated monoglycerides.
29. A composition, comprising:
50% to 99.9% by mass of one or more first compounds selected from the group consisting of fatty acids, fatty acid esters, fatty acid salts, and combinations thereof, wherein each of the one or more first compounds has a carbon chain length of at least 14; and
0.1 to 35% by mass of one or more second compounds selected from the group consisting of fatty acids, fatty acid esters, fatty acid salts, and combinations thereof, wherein each of the one or more second compounds has a carbon chain length in the range of 7 to 13.
30. The composition of claim 29, wherein each of the one or more second compounds has a carbon chain length of 8, 10, 11, or 12.
31. The composition of claim 29, wherein each of the one or more first compounds and each of the one or more second compounds is a compound of formula I or formula III, wherein formula I and formula III are:
Figure FDA0003045368930000391
wherein for each of the formulas:
R1、R2、R5、R6、R9、R10、R11、R12and R13Each occurrence of the formula is independently-H, - (C ═ O) R14、–(C=O)H、–(C=O)OH、–(C=O)OR14、–(C=O)-O-(C=O)R14、–O(C=O)R14、–OR14、–NR14R15、–SR14Halogen, -C1-C6Alkyl, -C2-C6Alkenyl, -C2-C6Alkynyl, -C3-C7Cycloalkyl, aryl OR heteroaryl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl OR heteroaryl is optionally substituted by one OR more-OR14、–NR14R15、–SR14Or halogen substitution;
R3、R4、R7and R8At each occurrence independently is-H, -OR14、–NR14R15、–SR14Halogen, -C1-C6Alkyl, -C2-C6Alkenyl, -C2-C6Alkynyl, -C3-C7Cycloalkyl, aryl OR heteroaryl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl OR heteroaryl is optionally substituted with-OR14、–NR14R15、–SR14Or halogen substitution; or
R3And R4May combine with the carbon atom to which they are attached to form C3-C6Cycloalkyl radical, C4-C6Cycloalkenyl or 3 to 6 membered ring heterocycle; and/or
R7And R8May combine with the carbon atom to which they are attached to form C3-C6Cycloalkyl radical, C4-C6Cycloalkenyl or 3 to 6 membered rings;
R14and R15Each occurrence independently is-H, aryl, heteroaryl, -C1-C6Alkyl, -C2-C6Alkenyl or-C2-C6An alkynyl group;
(symbol)
Figure FDA0003045368930000392
represents an optional single bond or a cis or trans double bond;
n is 0, 1,2, 3, 4, 5, 6, 7 or 8;
m is 0, 1,2 or 3;
q is 0, 1,2, 3, 4 or 5;
r is 0, 1,2, 3, 4, 5, 6, 7 or 8;
r is selected from-H, -glyceryl, -C1-C6Alkyl, -C2-C6Alkenyl, -C2-C6Alkynyl, -C3-C7Cycloalkyl, aryl or heteroaryl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl or heteroaryl is optionally substituted by one or more groups selected from halogen, hydroxy, nitro, -CN, -NH2、–SH、–SR15、–OR14、–NR14R15、–C1-C6Alkyl, -C2-C6Alkenyl or-C2-C6Radical substitution of alkynyl; and is
Xp+Is a cationic counterion having a charge state p, and p is 1,2 or 3.
32. The composition of claim 31, wherein the cationic counterion is an inorganic ion.
33. The composition of claim 31, wherein the cationic counterion is an organic ion.
34. A composition, comprising:
50% to 99.9% by mass of one or more first compounds selected from the group consisting of fatty acids, fatty acid esters, fatty acid salts, and combinations thereof, wherein each of the one or more first compounds has a carbon chain length of at least 14; and
0.1 to 35% by mass of one or more second compounds selected from the group consisting of phospholipids, lysophospholipids, glycoglycerolipids, glycolipids, ascorbates of fatty acids, esters of lactic acid, esters of tartaric acid, esters of malic acid, esters of fumaric acid, esters of succinic acid, esters of citric acid, esters of pantothenic acid, fatty alcohol derivatives, and combinations thereof.
35. The composition of any one of claims 29-34, wherein each of the one or more second compounds is a humectant.
36. The composition of any one of claims 29-34, wherein the one or more first compounds comprise one or more monoacylglycerides or fatty acid salts.
37. The composition of any one of claims 29-34, wherein the one or more first compounds is a combination of one or more monoacylglycerides and one or more fatty acid salts.
38. The composition according to claim 37, wherein the mass ratio of the monoacylglyceride to the fatty acid salt is in the range of about 2 to 100.
39. A composition, comprising:
from about 50% to about 99.8% by mass of one or more first compounds selected from the group consisting of fatty acids, fatty acid esters, and combinations thereof, wherein each compound of the first group has a carbon chain length of at least 14;
from about 0.1% to about 35% by mass of one or more humectants;
from about 0.1% to about 25% by mass of one or more fatty acid salts, wherein each fatty acid salt has a carbon chain length of at least 14.
40. The composition of claim 39, wherein each of the one or more first compounds is a compound of formula I:
Figure FDA0003045368930000411
wherein:
r is selected from-H, -glyceryl, -C1-C6Alkyl, -C2-C6Alkenyl, -C2-C6Alkynyl, -C3-C7Cycloalkyl, aryl or heteroaryl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl or heteroaryl is optionally substituted by one or more groups selected from halogen, hydroxy, nitro, -CN, -NH2、–SH、–SR15、–OR14、–NR14R15、–C1-C6Alkyl, -C2-C6Alkenyl or-C2-C6Radical substitution of alkynyl;
R1、R2、R5、R6、R9、R10、R11、R12and R13Each occurrence of the formula is independently-H, - (C ═ O) R14、–(C=O)H、–(C=O)OH、–(C=O)OR14、–(C=O)-O-(C=O)R14、–O(C=O)R14、–OR14、–NR14R15、–SR14Halogen, -C1-C6Alkyl, -C2-C6Alkenyl, -C2-C6Alkynyl, -C3-C7Cycloalkyl, aryl OR heteroaryl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl OR heteroaryl is optionally substituted by one OR more-OR14、–NR14R15、–SR14Or halogen substitution;
R3、R4、R7and R8At each occurrence independently is-H, -OR14、–NR14R15、–SR14Halogen, -C1-C6Alkyl, -C2-C6Alkenyl, -C2-C6Alkynyl, -C3-C7Cycloalkyl, aryl or heteroaryl, whereinEach alkyl, alkenyl, alkynyl, cycloalkyl, aryl OR heteroaryl group is optionally substituted with-OR14、–NR14R15、–SR14Or halogen substitution; or
R3And R4May combine with the carbon atom to which they are attached to form C3-C6Cycloalkyl radical, C4-C6Cycloalkenyl or 3 to 6 membered ring heterocycle; and/or
R7And R8May combine with the carbon atom to which they are attached to form C3-C6Cycloalkyl radical, C4-C6Cycloalkenyl or 3 to 6 membered rings;
R14and R15Each occurrence independently is-H, aryl, heteroaryl, -C1-C6Alkyl, -C2-C6Alkenyl or-C2-C6An alkynyl group;
(symbol)
Figure FDA0003045368930000412
represents an optional single bond or a cis or trans double bond;
n is 0, 1,2, 3, 4, 5, 6, 7 or 8;
m is 0, 1,2 or 3;
q is 0, 1,2, 3, 4 or 5; and is
r is 0, 1,2, 3, 4, 5, 6, 7 or 8.
41. The composition of any one of claims 39-40, wherein each of the one or more fatty acid salts is a compound of formula III, wherein formula III is:
Figure FDA0003045368930000421
wherein:
R1、R2、R5、R6、R9、R10、R11、R12and R13Each occurrence is independent of the otherImmediately under the name of-H, - (C ═ O) R14、–(C=O)H、–(C=O)OH、–(C=O)OR14、–(C=O)-O-(C=O)R14、–O(C=O)R14、–OR14、–NR14R15、–SR14Halogen, -C1-C6Alkyl, -C2-C6Alkenyl, -C2-C6Alkynyl, -C3-C7Cycloalkyl, aryl OR heteroaryl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl OR heteroaryl is optionally substituted by one OR more-OR14、–NR14R15、–SR14Or halogen substitution;
R3、R4、R7and R8At each occurrence independently is-H, -OR14、–NR14R15、–SR14Halogen, -C1-C6Alkyl, -C2-C6Alkenyl, -C2-C6Alkynyl, -C3-C7Cycloalkyl, aryl OR heteroaryl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl OR heteroaryl is optionally substituted with-OR14、–NR14R15、–SR14Or halogen substitution; or
R3And R4May combine with the carbon atom to which they are attached to form C3-C6Cycloalkyl radical, C4-C6Cycloalkenyl or 3 to 6 membered ring heterocycle; and/or
R7And R8May combine with the carbon atom to which they are attached to form C3-C6Cycloalkyl radical, C4-C6Cycloalkenyl or 3 to 6 membered rings;
R14and R15Each occurrence independently is-H, aryl, heteroaryl, -C1-C6Alkyl, -C2-C6Alkenyl or-C2-C6An alkynyl group;
(symbol)
Figure FDA0003045368930000422
represents an optional single bond or a cis or trans double bond;
n is 0, 1,2, 3, 4, 5, 6, 7 or 8;
m is 0, 1,2 or 3;
q is 0, 1,2, 3, 4 or 5;
r is 0, 1,2, 3, 4, 5, 6, 7 or 8; and is
Xp+Is a cationic counterion having a charge state p, and p is 1,2 or 3.
42. The composition of any one of claims 39-40, wherein each of the one or more first compounds comprises a fatty acid ester.
43. A composition according to claim 42, wherein each of the one or more first compounds comprises a monoacylglycerol.
44. The composition according to any one of claims 39-40, wherein the mass ratio of the one or more first compounds to the fatty acid salt is from 2 to 100.
45. The composition of any one of claims 39-40, wherein each of the one or more humectants is selected from the group consisting of fatty acids, fatty acid esters, and fatty acid salts, and each of the one or more humectants has a carbon chain length in the range of from 7 to 13.
46. The composition of claim 45, wherein each of the one or more humectants is a monoacylglycerol.
47. The composition of any one of claims 39-40, wherein each of the one or more humectants is selected from the group consisting of phospholipids, lysophospholipids, glycoglycerolipids, glycolipids, ascorbates of fatty acids, esters of lactic acid, esters of tartaric acid, esters of malic acid, esters of fumaric acid, esters of succinic acid, esters of citric acid, esters of pantothenic acid, and fatty alcohol derivatives.
48. A composition, comprising:
from about 50% to about 99.8% by mass of a first group of compounds, wherein each compound of the first group is a compound of formula I having a carbon chain length of at least 14;
from about 0.1% to about 35% by mass of a second group of compounds, wherein each compound of the second group is a compound of formula I having a carbon chain length in the range of from 7 to 13; and
from about 0.1% to about 25% by mass of a third group of compounds, wherein each compound of the third group is a salt of formula III, wherein formula I and formula III are:
Figure FDA0003045368930000431
wherein for each of the formulas:
R1、R2、R5、R6、R9、R10、R11、R12and R13Each occurrence of the formula is independently-H, - (C ═ O) R14、–(C=O)H、–(C=O)OH、–(C=O)OR14、–(C=O)-O-(C=O)R14、–O(C=O)R14、–OR14、–NR14R15、–SR14Halogen, -C1-C6Alkyl, -C2-C6Alkenyl, -C2-C6Alkynyl, -C3-C7Cycloalkyl, aryl OR heteroaryl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl OR heteroaryl is optionally substituted by one OR more-OR14、–NR14R15、–SR14Or halogen substitution;
R3、R4、R7and R8At each occurrence independently is-H, -OR14、–NR14R15、–SR14Halogen, halogen,–C1-C6Alkyl, -C2-C6Alkenyl, -C2-C6Alkynyl, -C3-C7Cycloalkyl, aryl OR heteroaryl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl OR heteroaryl is optionally substituted with-OR14、–NR14R15、–SR14Or halogen substitution; or
R3And R4May combine with the carbon atom to which they are attached to form C3-C6Cycloalkyl radical, C4-C6Cycloalkenyl or 3 to 6 membered ring heterocycle; and/or
R7And R8May combine with the carbon atom to which they are attached to form C3-C6Cycloalkyl radical, C4-C6Cycloalkenyl or 3 to 6 membered rings;
R14and R15Each occurrence independently is-H, aryl, heteroaryl, -C1-C6Alkyl, -C2-C6Alkenyl or-C2-C6An alkynyl group;
(symbol)
Figure FDA0003045368930000441
represents an optional single bond or a cis or trans double bond;
n is 0, 1,2, 3, 4, 5, 6, 7 or 8;
m is 0, 1,2 or 3;
q is 0, 1,2, 3, 4 or 5;
r is 0, 1,2, 3, 4, 5, 6, 7 or 8;
r is selected from-H, -glyceryl, -C1-C6Alkyl, -C2-C6Alkenyl, -C2-C6Alkynyl, -C3-C7Cycloalkyl, aryl or heteroaryl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl or heteroaryl is optionally substituted by one or more groups selected from halogen, hydroxy, nitro, -CN, -NH2、–SH、–SR15、–OR14、–NR14R15、–C1-C6Alkyl, -C2-C6Alkenyl or-C2-C6Radical substitution of alkynyl; and is
Xp+Is a cationic counterion having a charge state p, and p is 1,2 or 3.
49. The composition of claim 48, wherein each compound of the first group comprises a fatty acid or fatty acid ester.
50. The composition of claim 48, wherein each compound of the first group comprises a monoacylglycerol.
51. The composition of any one of claims 48-50, wherein the mass ratio of the first group of compounds to the third group of compounds is in the range of 2 to 100.
52. The composition of any one of claims 48-50, wherein the cationic moiety comprises sodium, potassium, calcium, or magnesium.
53. A mixture comprising the composition of any one of claims 29-52 in a solvent.
54. A mixture as claimed in claim 53, wherein said solvent is at least 70% water by volume.
55. A mixture as in any of claims 53-54, wherein said solvent further comprises ethanol.
56. The mixture of any one of claims 53-54, wherein the mixture further comprises an antimicrobial agent.
57. The mixture according to claim 56, wherein the antimicrobial agent comprises citric acid.
58. A mixture according to any one of claims 53-54, wherein the solvent is a hydrophilic solvent.
59. A mixture according to any one of claims 53-58, wherein the mixture further comprises sodium bicarbonate.
60. The mixture of any one of claims 53-54, wherein the concentration of the humectant in the mixture is at least about 0.1 mg/mL.
61. The mixture of any one of claims 53-54, wherein the concentration of the composition in the mixture is in the range of 0.5 to 200 mg/mL.
62. A mixture as claimed in claim 61, wherein said solvent is water.
63. A method of forming a mixture, comprising:
providing a solvent, wherein the solvent is characterized by exhibiting a contact angle of at least about 70 ° when placed on the surface of carnauba wax; and
adding a composition to the solvent to form the mixture; wherein
The composition comprises one or more fatty acids or salts or esters thereof; and is
The mixture is characterized by exhibiting a contact angle of less than about 65 ° when placed on the surface of carnauba wax.
64. The method of claim 63, wherein at least one of the fatty acids or salts or esters thereof of the composition has a carbon chain length of 13 or less.
65. The method of any one of claims 63-64, wherein at least one of the fatty acids or salts or esters thereof of the composition has a carbon chain length of 14 or greater.
66. The method of any one of claims 63-64, wherein the solvent is at least 70% water by volume.
67. The method of any one of claims 63-64, wherein the one or more fatty acids or salts or esters thereof are compounds of formula I or formula III, wherein formula I and formula III are:
Figure FDA0003045368930000451
wherein for each of the formulas:
R1、R2、R5、R6、R9、R10、R11、R12and R13Each occurrence of the formula is independently-H, - (C ═ O) R14、–(C=O)H、–(C=O)OH、–(C=O)OR14、–(C=O)-O-(C=O)R14、–O(C=O)R14、–OR14、–NR14R15、–SR14Halogen, -C1-C6Alkyl, -C2-C6Alkenyl, -C2-C6Alkynyl, -C3-C7Cycloalkyl, aryl OR heteroaryl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl OR heteroaryl is optionally substituted by one OR more-OR14、–NR14R15、–SR14Or halogen substitution;
R3、R4、R7and R8At each occurrence independently is-H, -OR14、–NR14R15、–SR14Halogen, -C1-C6Alkyl, -C2-C6Alkenyl, -C2-C6Alkynyl, -C3-C7Cycloalkyl, aryl OR heteroaryl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl OR heteroaryl is optionally substituted with-OR14、–NR14R15、–SR14Or halogen substitution; or
R3And R4May combine with the carbon atom to which they are attached to form C3-C6Cycloalkyl radical, C4-C6Cycloalkenyl or 3 to 6 membered ring heterocycle; and/or
R7And R8May combine with the carbon atom to which they are attached to form C3-C6Cycloalkyl radical, C4-C6Cycloalkenyl or 3 to 6 membered rings;
R14and R15Each occurrence independently is-H, aryl, heteroaryl, -C1-C6Alkyl, -C2-C6Alkenyl or-C2-C6An alkynyl group;
(symbol)
Figure FDA0003045368930000461
represents an optional single bond or a cis or trans double bond;
n is 0, 1,2, 3, 4, 5, 6, 7 or 8;
m is 0, 1,2 or 3;
q is 0, 1,2, 3, 4 or 5;
r is 0, 1,2, 3, 4, 5, 6, 7 or 8;
r is selected from-H, -glyceryl, -C1-C6Alkyl, -C2-C6Alkenyl, -C2-C6Alkynyl, -C3-C7Cycloalkyl, aryl or heteroaryl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl or heteroaryl is optionally substituted by one or more groups selected from halogen, hydroxy, nitro, -CN, -NH2、–SH、–SR15、–OR14、–NR14R15、–C1-C6Alkyl, -C2-C6Alkenyl or-C2-C6Radical substitution of alkynyl; and is
Xp+Is a cationic counterion having a charge state p, and p is 1,2 or 3.
68. A composition, comprising:
from about 50% to about 99% by mass of one or more fatty acid esters having a carbon chain length of at least 14; and
about 1% to about 50% by mass of one or more salts of fatty acids having a carbon chain length of at least 14.
69. The composition of claim 68, wherein the one or more fatty acid esters comprise one or more monoacylglycerides.
70. The composition according to any one of claims 68-69, wherein the mass ratio of the one or more fatty acid esters to the one or more fatty acid salts is in the range of about 2 to 99.
71. The composition of any one of claims 68-70, wherein the composition comprises less than 10% diglycerides by mass.
72. The composition of any one of claims 68-71, wherein the composition comprises less than 10% triglycerides by mass.
73. The composition according to any one of claims 68-72, wherein the composition comprises less than 10% by mass of acetylated monoglycerides.
74. A mixture comprising the composition of any one of claims 68-73 in a solvent.
75. A method of treating an agricultural product, the method comprising coating the agricultural product with a composition comprising:
(i) from about 50% to about 99.9% by mass of one or more first compounds selected from the group consisting of fatty acids, fatty acid esters, fatty acid salts, and combinations thereof, wherein each of the one or more first compounds has a carbon chain length of at least 14; and
(ii) from about 0.1% to about 35% by mass of one or more second compounds selected from the group consisting of fatty acids, fatty acid esters, fatty acid salts, and combinations thereof, wherein each of the one or more second compounds has a carbon chain length in the range of from 7 to 13.
76. The method of claim 75, wherein each of the one or more second compounds has a carbon chain length of 8, 10, 11, or 12.
77. A method of treating an agricultural product, the method comprising coating the agricultural product with a composition comprising:
(i) from about 50% to about 99.8% by mass of one or more first compounds selected from the group consisting of fatty acids, fatty acid esters, and combinations thereof, wherein each compound of the first group has a carbon chain length of at least 14;
(ii) from about 0.1% to about 35% by mass of one or more humectants;
(iii) from about 0.1% to about 25% by mass of one or more fatty acid salts, wherein each fatty acid salt has a carbon chain length of at least 14.
78. The method of claim 77, wherein each of said one or more wetting agents is selected from the group consisting of fatty acids, fatty acid esters, and fatty acid salts, and each of said one or more wetting agents has a carbon chain length in the range of 7 to 13.
79. The method of claim 78, wherein each of the one or more humectants is a monoacylglyceride.
80. The method of claim 77, wherein each of the one or more humectants is selected from the group consisting of a phospholipid, a lysophospholipid, a glycoglycerolipid, a glycolipid, an ascorbic acid ester of a fatty acid, an ester of lactic acid, an ester of tartaric acid, an ester of malic acid, an ester of fumaric acid, an ester of succinic acid, an ester of citric acid, an ester of pantothenic acid, and a fatty alcohol derivative.
81. The method of any one of claims 75-80, wherein each of the one or more first compounds is a compound of formula I:
Figure FDA0003045368930000481
wherein:
r is selected from-H, -glyceryl, -C1-C6Alkyl, -C2-C6Alkenyl, -C2-C6Alkynyl, -C3-C7Cycloalkyl, aryl or heteroaryl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl or heteroaryl is optionally substituted with one or more substituents selected from halogen (e.g., Cl, Br or I), hydroxy, nitro, -CN, -NH2、–SH、–SR15、–OR14、–NR14R15、–C1-C6Alkyl, -C2-C6Alkenyl or-C2-C6Radical substitution of alkynyl;
R1、R2、R5、R6、R9、R10、R11、R12and R13Each occurrence independently is-H,
–(C=O)R14、–(C=O)H、–(C=O)OH、–(C=O)OR14、–(C=O)-O-(C=O)R14、–O(C=O)R14、–OR14、–NR14R15、–SR14Halogen, -C1-C6Alkyl, -C2-C6Alkenyl, -C2-C6Alkynyl, -C3-C7Cycloalkyl, aryl OR heteroaryl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl OR heteroaryl is optionally substituted by one OR more-OR14、–NR14R15、–SR14Or halogen substitution;
R3、R4、R7and R8At each occurrence independently is-H, -OR14、–NR14R15、–SR14Halogen, -C1-C6Alkyl, -C2-C6Alkenyl, -C2-C6Alkynyl, -C3-C7Cycloalkyl, aryl OR heteroaryl, wherein each alkyl, alkynyl, cycloalkyl, aryl OR heteroaryl is optionally substituted by one OR more-OR14、–NR14R15、–SR14Or halogen substitution; or
R3And R4May combine with the carbon atom to which they are attached to form C3-C6Cycloalkyl radical, C4-C6Cycloalkenyl or 3 to 6 membered ring heterocycle; and/or
R7And R8May combine with the carbon atom to which they are attached to form C3-C6Cycloalkyl radical, C4-C6Cycloalkenyl or 3 to 6 membered ring heterocycle;
R14and R15Each occurrence independently is-H, aryl, heteroaryl, -C1-C6Alkyl, -C2-C6Alkenyl or-C2-C6An alkynyl group;
(symbol)
Figure FDA0003045368930000482
represents a single bond or a cis-or trans-double bond;
n is 0, 1,2, 3, 4, 5, 6, 7 or 8;
m is 0, 1,2 or 3;
q is 0, 1,2, 3, 4 or 5; and is
r is 0, 1,2, 3, 4, 5, 6, 7 or 8.
82. The method of any one of claims 75-80, wherein the one or more first compounds comprise one or more monoacylglycerides or fatty acid salts.
83. The method of any one of claims 75-80, wherein the one or more first compounds is a combination of one or more monoacylglycerides and one or more fatty acid salts.
84. The method of claim 83, wherein the mass ratio of the monoacylglyceride to the fatty acid salt is in the range of about 2 to 100.
85. A method of treating an agricultural product, the method comprising coating the agricultural product with a composition comprising:
(i) from about 50% to about 99% by mass of one or more fatty acid esters having a carbon chain length of at least 14; and
(ii) about 1% to about 50% by mass of one or more salts of fatty acids having a carbon chain length of at least 14.
86. The method of any one of claims 75-80 and 85, wherein the composition comprises an antimicrobial agent.
87. The method of any one of claims 75-80 and 85, wherein the composition further comprises one or more additives.
88. The method of claim 87, wherein the one or more additives is a pH adjuster.
89. The method of claim 88, wherein the pH adjusting agent is sodium bicarbonate.
90. The method of any one of claims 75-80 and 85, wherein the composition is dissolved or dispersed in a solvent and the resulting solution, suspension or colloid is applied to the agricultural product.
91. The method of claim 90, wherein the solvent is a hydrophilic solvent.
92. The method of claim 90, wherein the solvent is at least 70% water by volume.
93. The method of claim 92, wherein the solvent further comprises ethanol.
94. The method of any one of claims 75-80 and 85, wherein the agricultural product is coated with the composition by spraying.
95. The method of any one of claims 75-80 and 85, wherein the agricultural product is coated with the composition by dipping.
96. The method of any one of claims 75-80 and 85, wherein the agricultural product is coated with the composition by brushing.
97. The method of any one of claims 75-80 and 85, wherein the coating reduces the amount of heat generated by respiration of the agricultural product.
98. The method of any one of claims 75-80 and 85, wherein the agricultural product comprises fresh fruit, fresh vegetables, or a combination thereof.
99. The method of any one of claims 75-80 and 85, wherein the agricultural product comprises a flower or cut flower.
100. A method for reducing the heat generated by respiration of an agricultural product, the method comprising coating the agricultural product with a composition, wherein the coating reduces the average respiration rate of the agricultural product by at least about 10%.
101. The method of claim 100, wherein the coating reduces the average respiration rate of the agricultural product by at least 15%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75%, 80%, 85%, or 90%.
102. The method of claim 100, wherein the composition comprises:
(i) from about 50% to about 99.9% by mass of one or more first compounds selected from the group consisting of fatty acids, fatty acid esters, fatty acid salts, and combinations thereof, wherein each of the one or more first compounds has a carbon chain length of at least 14; and
(ii) from about 0.1% to about 35% by mass of one or more second compounds selected from the group consisting of fatty acids, fatty acid esters, fatty acid salts, and combinations thereof, wherein each of the one or more second compounds has a carbon chain length in the range of from 7 to 13.
103. The method of claim 102, wherein each of the one or more second compounds has a carbon chain length of 8, 10, 11, or 12.
104. The method of claim 100, wherein the composition comprises:
(i) from about 50% to about 99.8% by mass of one or more first compounds selected from the group consisting of fatty acids, fatty acid esters, and combinations thereof, wherein each compound of the first group has a carbon chain length of at least 14;
(ii) from about 0.1% to about 35% by mass of one or more humectants;
(iii) from about 0.1% to about 25% by mass of one or more fatty acid salts, wherein each fatty acid salt has a carbon chain length of at least 14.
105. The method of claim 104, wherein each of said one or more humectants is selected from the group consisting of fatty acids, fatty acid esters, and fatty acid salts, and each of said one or more humectants has a carbon chain length in the range of from 7 to 13.
106. The method of claim 105, wherein each of the one or more humectants is a monoacylglyceride.
107. The method of claim 104, wherein each of the one or more humectants is selected from the group consisting of a phospholipid, a lysophospholipid, a glycoglycerolipid, a glycolipid, an ascorbic acid ester of a fatty acid, an ester of lactic acid, an ester of tartaric acid, an ester of malic acid, an ester of fumaric acid, an ester of succinic acid, an ester of citric acid, an ester of pantothenic acid, and a fatty alcohol derivative.
108. The method of any one of claims 102-107, wherein each of the one or more first compounds is a compound of formula I:
Figure FDA0003045368930000511
wherein:
r is selected from-H, -glyceryl, -C1-C6Alkyl, -C2-C6Alkenyl, -C2-C6Alkynyl, -C3-C7Cycloalkyl, aryl or heteroaryl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl or heteroaryl is optionally substituted with one or more substituents selected from halogen (e.g., Cl, Br or I), hydroxy, nitro, -CN, -NH2、–SH、–SR15、–OR14、–NR14R15、–C1-C6Alkyl, -C2-C6Alkenyl or-C2-C6Radical substitution of alkynyl;
R1、R2、R5、R6、R9、R10、R11、R12and R13Each occurrence independently is-H,
–(C=O)R14、–(C=O)H、–(C=O)OH、–(C=O)OR14、–(C=O)-O-(C=O)R14、–O(C=O)R14、–OR14、–NR14R15、–SR14Halogen, -C1-C6Alkyl, -C2-C6Alkenyl, -C2-C6Alkynyl, -C3-C7Cycloalkyl, aryl OR heteroaryl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl OR heteroaryl is optionally substituted by one OR more-OR14、–NR14R15、–SR14Or halogen substitution;
R3、R4、R7and R8At each occurrence independently is-H, -OR14、–NR14R15、–SR14Halogen, -C1-C6Alkyl, -C2-C6Alkenyl, -C2-C6Alkynyl, -C3-C7Cycloalkyl, aryl OR heteroaryl, wherein each alkyl, alkynyl, cycloalkyl, aryl OR heteroaryl is optionally substituted by one OR more-OR14、–NR14R15、–SR14Or halogen substitution; or
R3And R4May combine with the carbon atom to which they are attached to form C3-C6Cycloalkyl radical, C4-C6Cycloalkenyl or 3 to 6 membered ring heterocycle; and/or
R7And R8May combine with the carbon atom to which they are attached to form C3-C6Cycloalkyl radical, C4-C6Cycloalkenyl or 3 to 6 membered ring heterocycle;
R14and R15Each occurrence independently is-H, aryl, heteroaryl, -C1-C6Alkyl, -C2-C6Alkenyl or-C2-C6An alkynyl group;
(symbol)
Figure FDA0003045368930000512
represents a single bond or a cis-or trans-double bond;
n is 0, 1,2, 3, 4, 5, 6, 7 or 8;
m is 0, 1,2 or 3;
q is 0, 1,2, 3, 4 or 5; and is
r is 0, 1,2, 3, 4, 5, 6, 7 or 8.
109. The method of any one of claims 102-107, wherein the one or more first compounds comprise one or more monoacylglycerides or fatty acid salts.
110. The method of any one of claims 102-107, wherein the one or more first compounds is a combination of one or more monoacylglycerides and one or more fatty acid salts.
111. The method of claim 110 wherein the mass ratio of the monoacylglyceride to the fatty acid salt is in the range of about 2 to 100.
112. The method of claim 100, wherein the composition comprises:
(i) from about 50% to about 99% by mass of one or more fatty acid esters having a carbon chain length of at least 14; and
(ii) about 1% to about 50% by mass of one or more salts of fatty acids having a carbon chain length of at least 14.
113. The method of any one of claims 102 and 107 and 112, wherein the composition comprises an antimicrobial agent.
114. The method of any one of claims 102 and 107 and 112, wherein the composition further comprises one or more additives.
115. The method of claim 114, wherein the one or more additives is a pH adjuster.
116. The method of claim 115, wherein the pH adjusting agent is sodium bicarbonate.
117. The method as set forth in any one of claims 102 and 107 to 112 wherein the composition is dissolved or dispersed in a solvent and the resulting solution, suspension or colloid is applied to the agricultural product.
118. The method of claim 117, wherein the solvent is a hydrophilic solvent.
119. The method of claim 117, wherein the solvent is at least 70% water by volume.
120. The method of claim 119, wherein the solvent further comprises ethanol.
121. The method as set forth in any one of claims 102 and 107 to 112 wherein the agricultural product is coated with the composition by spraying.
122. The method as set forth in any one of claims 102 and 107 to 112 wherein the agricultural product is coated with the composition by dipping.
123. The method as set forth in any one of claims 102 and 107 to 112 wherein the agricultural product is coated with the composition by brushing.
124. The method of claim 123, wherein the brushing is performed using a brush bed.
125. The method of any one of claims 102 and 107 and 112, wherein the agricultural product comprises fresh fruit, fresh vegetables, or a combination thereof.
126. The method as set forth in any one of claims 102 and 107 to 112 wherein the agricultural product comprises a flower or cut flower.
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